0000000001301996
AUTHOR
Kirsi Salorinne
Hydrophobic pocket targeting probes for enteroviruses
Visualization and tracking of viruses without compromising their functionality is crucial in order to understand virus targeting to cells and tissues, and to understand the subsequent subcellular steps leading to virus uncoating and replication. Enteroviruses are important human pathogens causing a vast number of acute infections, and are also suggested to contribute to the development of chronic diseases like type I diabetes. Here, we demonstrate a novel method to target site-specifically the hydrophobic pocket of enteroviruses. A probe, a derivative of Pleconaril, was developed and conjugated to various labels that enabled the visualization of enteroviruses under light and electron micros…
Synthesis and structure of mono-bridged resorcinarene host: a ditopic receptor for ammonium guests.
The synthesis and structural properties of tetramethoxy resorcinarene mono-crown-5 (1) are described. The binding characteristics of 1 toward acetylcholine and tetramethylammonium salts were investigated by 1H NMR titration. It was observed that the cavity of 1 provides a better fit to acetylcholine compared to the smaller tetramethylammonium cation, as acetylcholine is able to interact with both the crown ether moiety and the free hydroxyl groups of receptor 1 simultaneously.
The Structural Diversity of Benzofuran Resorcinarene Leads to Enhanced Fluorescence
An unexpected and previously unknown resorcinarene mono-crown with a fused benzofuran moiety in its macrocyclic core was obtained as a byproduct from a bridging reaction of tetramethoxy resorcinarene with tetraethylene glycol ditosylate. The formation of the fused benzofuran moiety in the resorcinarene macrocycle resulted in a unique rigid and puckered boat conformation, as shown by XRD studies in the solid state. Modification of the macrocycle was also observed to affect the photophysical properties in solution by enhancing the fluorescence brightness compared with a conventional resorcinarene macrocycle. The fluorescent properties enabled unique detection of structural features, that is, …
Photodynamics of a Molecular Water-Soluble Nanocluster Identified as Au130(pMBA)50
Photodynamics of a highly monodisperse sample of a water-soluble gold nanocluster tentatively identified as Au130(pMBA)50 (pMBA = p-mercaptobenzoic acid) was studied by mid-IR transient absorption spectroscopy with visible excitation. The observed long-lived excited states (>1 ns) indicate a molecular behavior of the cluster. By combining the transient absorption data with DFT calculation results the observed relaxation dynamics could be fully explained by identifying several relaxation processes involving singlet and triplet manifolds. The results indicate that the cluster may have interesting transient magnetic properties due to a long-lived triplet population.
Development of functionalized SYBR green II related cyanine dyes for viral RNA detection
Fluorescent probes for sensing nucleic acids have found widespread use in the field of cell and molecular biology. However, probes combined with potential for post-synthetic conjugation, e.g. for intra-endosomal measurements of RNA, are unavailable. Herein we developed cyanine dyes that can be conjugated to viral capsid or other targets. First, we solved the crystal structure of SYBR Green II. The structural elucidation of this commonly used RNA probe provided the basis for synthesizing similar molecules with much desired function for post-synthetic conjugation. To address this need, cyanine dyes were prepared using an alternative synthesis protocol. All studied compounds showed considerabl…
Molecule-like photodynamics of Au102(pMBA)44 nanocluster.
Photophysical properties of a water-soluble cluster Au102(pMBA)44 (pMBA = para-mercaptobenzoic acid) are studied by ultrafast time-resolved mid-IR spectroscopy and density functional theory calculations in order to distinguish between molecular and metallic behavior. In the mid-IR transient absorption studies, visible or near-infrared light is used to electronically excite the sample, and the subsequent relaxation is monitored by studying the transient absorption of a vibrational mode in the ligands. Based on these studies, a complete picture of energy relaxation dynamics is obtained: (1) 0.5-1.5 ps electronic relaxation, (2) 6.8 ps vibrational cooling, (3) intersystem crossing from the low…
Resorcinarene Podand with Amine-Functionalized Side Arms â Synthesis, Structure, and Binding Properties of a Neutral Anion Receptor
The synthesis and structure of a neutral resorcinarene host bearing four amine-functionalized side arms is described. The anion binding properties were investigated in solution by 1H NMR spectroscopic titration and diffusion experiments and in the gas phase by mass spectrometric studies. It was observed that in solution 1:2 (host/guest) complexes were formed between the resorcinarene host and the basic fluoride and acetate anions, whereas in the gas phase 1:1 complexes with other anions (Cl–, HCOO–, NO3–, and BF4–) were detected additionally. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Structural analysis of two foldamer-type oligoamides – the effect of hydrogen bonding on solvate formation, crystal structures and molecular conformation
Author's Final draft The crystal structures and molecular conformations of two foldamer-type oligoamides were analyzed. One polymorphic form and seven solvates were found for N¹,N³-bis(2-benzamidophenyl)benzene-1,3-dicarboxamide (the benzene variant), and two polymorphic forms and six solvates for N²,N⁶-bis(2-benzamidophenyl)pyridine-2,6-dicarboxamide (the pyridine variant). Three crystal structures of the benzene variant and seven structures of the pyridine variant were solved using single crystal X-ray diffraction. The crystal structures showed that the different modes of intramolecular hydrogen bonding strongly affect the conformation and folding of the molecules, which is most evidently…
Asymmetric Homoaldol Reactions with Cyclohex-2-enylN,N-Diisopropylcarbamate: Kinetic Resolution, Elucidation of the Stereochemical Course and Applications in the Synthesis of Hexahydroisobenzofuran-4-(1H)-ones
Enantio-enriched cyclohex-2-enyl N,N-diisopropylcarbamate (5) is stereospecifically deprotonated by sec-butyllithium/(–)-sparteine (9) to form the configurationally stable lithium complex 7·9. A kinetic resolution of rac-5 by n-butyllithium/(–)-sparteine (9) yielded (R)-5 with up to 99 % ee. Electrophilic substitution with tin electrophiles proceeds in a anti-SE′ fashion as shown by chemical correlations. The synthesized allylstannanes 10 undergo a highly stereospecific TiCl4-mediated homoaldol reaction with various aldehydes, yielding syn-configured homoaldol products 12. These were transferred into all-cis-configured hexahydroisobenzofuran-4(1H)-ones 22 by BF3·OEt2-mediated reactions with…
Nondestructive Size Determination of Thiol-Stabilized Gold Nanoclusters in Solution by Diffusion Ordered NMR Spectroscopy
Diffusion ordered NMR spectroscopy (DOSY) was used as an analytical tool to estimate the size of thiol-stabilized gold nanoclusters in solution, namely, phenylethanethiol (PET) stabilized Au25(PET)18, Au38(PET)24, and Au144(PET)60. This was achieved by determining the diffusion coefficient and hydrodynamic radius from solution samples that were confirmed to be monodispersed by electrospray ionization mass spectrometry. The average cluster diameters obtained by this technique were estimated to be 1.7, 2.2, and 3.1 nm for the Au25(PET)18, Au38(PET)24, and Au144(PET)60 nanoclusters, respectively, which were shown to agree well with the average diameters of the corresponding single crystal or t…
Conformation and dynamics of the ligand shell of a water-soluble Au102 nanoparticle
Inorganic nanoparticles, stabilized by a passivating layer of organic molecules, form a versatile class of nanostructured materials with potential applications in material chemistry, nanoscale physics, nanomedicine and structural biology. While the structure of the nanoparticle core is often known to atomic precision, gaining precise structural and dynamical information on the organic layer poses a major challenge. Here we report a full assignment of 1H and 13C NMR shifts to all ligands of a water-soluble, atomically precise, 102-atom gold nanoparticle stabilized by 44 para-mercaptobenzoic acid ligands in solution, by using a combination of multidimensional NMR methods, density functional t…
Resorcinarene Bis-Thiacrowns: Prospective Host Molecules for Silver Encapsulation
Mixed-donor atom tetramethoxy resorcinarene bis-thiacrown hosts, in which the crown unit contains both hard oxygen and soft sulfur donor atoms, were synthesized for soft metal cation binding. The binding properties were investigated both in solution and in the solid state by NMR spectroscopy and X-ray crystallography. It was found that the resorcinarene bis-thiacrowns were able to complex silver cations with remarkable affinity forming readily 1:2 host–guest complexes in solution. The solid state structures also revealed that the bis-thiacrowns form silver complexes in an unanticipated endo- and exo-cavity fashion within the same host molecule. Both the solution and solid state studies indi…
The Missing Member of the Partially O-Alkylated Resorcinarene Family: Synthesis and Conformation of Methyl Tetramethoxy Resorcinarene
An improved Lewis acid catalyzed synthesis method for methyl tetramethoxy resorcinarene is described, which produced the missing lower rim methyl derivative of this partially O-alkylated resorcinarene family. Structural characterization by means of variable temperature NMR experiments and single crystal X-ray diffraction studies furthermore revealed that the resorcinarene core adopts different conformations in the solid state and in solution. peerReviewed
Solvent driven formation of silver embedded resorcinarene nanorods
Silver complexes of resorcinarene bis-crown-5 were observed to arrange into nanorods of 2.4 nm in diameter. The left- and right-handed isomers of the inherently chiral resorcinarene host are separated into their own entity in the self-assembly process with the periphery of the nanorods consisting of silver cations included in the cavity.
Solid state halogen bonded networks vs. dynamic assemblies in solution: explaining N⋯X interactions of multivalent building blocks
Tetrapyridine functionalized resorcinarene macrocycles were used as multivalent building blocks for the construction of halogen bonded networks with aryl halide linkers. In the solid state, resorcinarene macrocycles and aryl halide linker molecules assembled into interpenetrated, multidimensional halogen bonded networks with porous structure caused by the 3D block scaffold of the resorcinarenes. 19F NMR spectroscopy proved halogen bond formation also in solution, as either upfield or downfield shifts were observed depending on the bivalent or monovalent halogen bond binding mode. The binding mode in solution was explained by density functional theory computations. peerReviewed
Twisting of the resorcinarene core due to solvent effects upon crystallization
The effect of the crystallization conditions on the conformation of the tetramethoxy resorcinarene skeleton was investigated in acetone solutions, to which was added a second component (less favorable solvent or salt) to promote crystallization. The resorcinarene core was found to adopt three different conformations: crown (I), a pinched crown (II) and a twisted pinched crown (III). In addition, the flexibility of the resorcinarene core was compared with a tetramethoxy resorcinarene derivative, resorcinarene bis-crown, which is in a fixed boat conformation.
ChemInform Abstract: Calixcrowns : Synthesis and Properties
The synthesis and properties of calix[n]crowns (n = 4–8), calix[n]biscrowns and their related compounds, resorcinarene crowns, have been discussed and reviewed. These macrocycles exhibit remarkable ionophoric properties toward alkali and alkaline earth metal cations, as well as, to tertiary amines. The selectivity and efficiency of calixcrowns in binding cations have been attributed to their structural features, which include substituent effects and size of the crown ether moiety and, conformation of the parent calixarene.
Synthesis and Characterization of theO-Alkylation Products of Resorcinarene
O-Substitution reactions of tetramethoxyresorcinarene with alkyl halides produced a variety of partially O-alkylated resorcinarene derivatives with terminal alkyne functionality. The degree of alkylation was affected by the reactivity of the alkylating halide used. NMR spectroscopy proved to be an ideal tool for analyzing the complex reaction mixtures and the isolated products based on the symmetry and degree of alkylation of the resorcinarene derivatives. Single-crystal X-ray diffraction studies furthermore showed diversity in the self-assembly of the various O-alkylation products that was greatly affected by the degree of alkylation, as well as the nature of the alkyne moiety.
Development of functionalized SYBR green II related cyanine dyes for viral RNA detection
Abstract Fluorescent probes for sensing nucleic acids have found widespread use in the field of cell and molecular biology. However, probes combined with potential for post-synthetic conjugation, e.g. for intra-endosomal measurements of RNA, are unavailable. Herein we developed cyanine dyes that can be conjugated to viral capsid or other targets. First, we solved the crystal structure of SYBR Green II. The structural elucidation of this commonly used RNA probe provided the basis for synthesizing similar molecules with much desired function for post-synthetic conjugation. To address this need, cyanine dyes were prepared using an alternative synthesis protocol. All studied compounds showed co…
Synthesis and properties of an Au6 cluster supported by a mixed N-heterocyclic carbene–thiolate ligand
The preparation of a novel Au6 cluster bearing a bidentate mixed carbene–thiolate ligand is presented. The length of linker between the central benzimidazole and thiolate has a strong effect on the formation of cluster products, with a C2 chain giving an Au6 cluster, while a C3 chain results in no evidence of cluster formation. Density functional theory analysis predicts a non-metallic cluster with a large HOMO–LUMO (3.2–3.6 eV) and optical gap.
Crystal structure of 5-{3-[2,6-dimethyl- 4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}- N-(11-hydroxyundecyl)isoxazole-3-carboxamide hemihydrate
The crystal structure and supramolecular features of 5-{3-[2,6-dimethyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-N-(11-hydroxyundecyl)isoxazole-3-carboxamide hemihydrate, a derivative of antiviral ‘WIN compounds’, are reported.
Cation binding resorcinarene bis-crowns: the effect of lower rim alkyl chain length on crystal packing and solid lipid nanoparticles
A group of seven resorcinarene bis-crown ethers (CNBC5) with two polyether bridges at the upper rim and either propyl, butyl, pentyl, heptyl, nonyl, decyl or undecyl groups at the lower rim were synthesized and their binding properties with Cs+ were investigated by NMR titration. The bis-crowns form 1:2 complexes with Cs+ with binding constants of logK 4–5. Crystal structures of bis-crowns and their Cs+ and K+ complexes were studied and different packing motifs were found depending on the alkyl chain length. Short ethyl, propyl and butyl alkyl chains gave a layer or pillar packing where the polar and non-polar regions cannot be distinguished, whereas longer pentyl and decyl chains formed bi…
Ultrafast electronic relaxation and vibrational cooling dynamics of Au 144(SC2H4Ph)60 nanocluster probed by transient mid-IR spectroscopy
Energy relaxation dynamics of a gold nanocluster with atomically precise composition, Au144(SC2H4Ph)60, is studied by transient mid-IR spectroscopy. The experiment is designed to simultaneously pro...
The Effect of Halogen Bonding on the Packing of Bromine Substituted Pyridine and Benzyl Functionalized Resorcinarene Tetrapodands in the Solid State
The synthesis and characterization of new bromine-substituted pyridine and benzyl functionalized tetramethoxy resorcinarene tetrapodands are described and their solid-state structural properties and interactions were studied by single crystal X-ray crystallography. Three different crystal structures were obtained for the pyridine derivative and one for the benzyl derivative, which revealed that the interactions of the bromine substituent have an explicit effect on the crystal packing of the resorcinarene molecules. One of the structures obtained had very interesting halogen–halogen interactions with the same geometry as is generally found for compounds used in nonlinear optical studies. pee…
Site-specific targeting of enterovirus capsid by functionalized monodisperse gold nanoclusters
Development of precise protocols for accurate site-specific conjugation of monodisperse inorganic nanoparticles to biological material is one of the challenges in contemporary bionanoscience and nanomedicine. We report here a successful site-specific covalent conjugation of functionalized atomically monodisperse gold clusters with 1.5-nm metal cores to viral surfaces. Water-soluble Au102(para-mercaptobenzoic acid)44 clusters, functionalized by maleimide linkers to target cysteines of viral capsid proteins, were synthesized and conjugated to enteroviruses echovirus 1 and coxsackievirus B3. Quantitative analysis of transmission electron microscopy images and the known virus structures showed …
Jahn–Teller effects in Au25(SR)18
The relationship between oxidation state, structure, and magnetism in many molecules is well described by first-order Jahn–Teller distortions. This relationship is not yet well defined for ligated nanoclusters and nanoparticles, especially the nano-technologically relevant gold-thiolate protected metal clusters. Here we interrogate the relationships between structure, magnetism, and oxidation state for the three stable oxidation states, −1, 0 and +1 of the thiolate protected nanocluster Au25(SR)18. We present the single crystal X-ray structures of the previously undetermined charge state Au25(SR)18+1, as well as a higher quality single crystal structure of the neutral compound Au25(SR)180. …
The Effect of Halogen Bonding on the Packing of Bromine Substituted Pyridine and Benzyl Functionalized Resorcinarene Tetrapodands in the Solid State
The synthesis and characterization of new bromine-substituted pyridine and benzyl functionalized tetramethoxy resorcinarene tetrapodands are described and their solid-state structural properties and interactions were studied by single crystal X-ray crystallography. Three different crystal structures were obtained for the pyridine derivative and one for the benzyl derivative, which revealed that the interactions of the bromine substituent have an explicit effect on the crystal packing of the resorcinarene molecules. One of the structures obtained had very interesting halogen–halogen interactions with the same geometry as is generally found for compounds used in nonlinear optical studies.
Solvation chemistry of water-soluble thiol-protected gold nanocluster Au102 from DOSY NMR spectroscopy and DFT calculations
The hydrodynamic diameter of Aum(pMBA)n [(m, n) = (102, 44) and (144, 60)] clusters in aqueous media was determined via DOSY NMR spectroscopy. The apparent size of the same (n, m) cluster depends on the counter ion of the deprotonated pMBA− ligand as explained by the competing ion-pair strength and hydrogen bonding interactions studied in DFT calculations. The choice of the counter ion affects the surface chemistry and molecular structure at the organic/water interface, which is relevant for biological applications.
Novel Tetramethoxy Resorcinarene Bis-Crown Ethers
The synthesis and characterization of new tetramethoxy resorcinarene bis-crown ethers BC4 and BC5 are described. The complexation properties of the compounds toward alkali metal cations were studied by 1H NMR spectroscopy and X-ray crystallography, which revealed that BC5 can accommodate two cations simultaneously inside the crown pockets formed by the crown ether bridges and the resorcinarene skeleton. [reaction: see text].
Characterization and synthesis of O- and N-tosylated N,N-bis(2-aminophenyl)isophthalamide based ligands
Abstract A synthetic strategy for the preparation of O - and N- tosylated N , N -bis(2-aminophenyl)isophthalamide based ligands is described. It was observed that selectivity in O - and N -tosylation could be achieved by performing the reaction at low temperatures in the presence of an appropriate base. The obtained O - and N -tosylated products were characterized by means of NMR and mass spectroscopy, and X-ray crystallography.
Polymorphic and solvate structures of ethyl ester and carboxylic acid derivatives of WIN 61893 analogue and their stability in solution
3-Ethyl ester- (1) and 3-carboxylic acid-isoxazole (2) derivatives of an antiviral drug analogue WIN 61893 were synthesized and characterized by X-ray crystallography and NMR spectroscopy. Crystallization experiments afforded two polymorphic structures for the ethyl ester derivative and two solvate structures for the carboxylic acid derivative based on their ability to form intermolecular hydrogen bonding interactions with the solvent molecules. The conformations of the derivatives depended greatly on the orientation of the planar isoxazole and phenyl-oxadiazole ring systems with respect to one another and were found to take up perpendicular, linear or tilted conformations. The carboxylic a…
Alkali metal complexation properties of resorcinarene bis-crown ethers: effect of the crown ether functionality and preorganization on complexation
Abstract The synthesis and characterization of tetramethoxy resorcinarene tribenzo-bis-crown ethers, m - and p -TBBC6 , are described. The effect of the added aromatic functionality in the crown ether bridge on the alkali metal complexation properties was investigated and compared to the properties of tetramethoxy resorcinarene bis-crown-5 ( BC5 ) by means of 1 H NMR spectroscopy and X-ray crystallography. It was found that BC5 and m -TBBC6 were capable of binding alkali metal cations (K + , Rb + , and Cs + ), with the highest affinity toward Cs + cation, while no binding was observed in the case of p -TBBC6 , which confirms the significance of the complementarity and preorganization for co…
4,4-Di-fluoro-2,3;5,6-bis-(tetra-methylene)-4-bora-3a,4a-di-aza-s-indacene (LD540).
The title compound, C18H21BF2N2, is a lipophilic dye based on a BODIPY fluorophore backbone, which was developed for microscopic imaging of lipid droplets; the molecule has a planar BODIPY core [dihedral angle between the pyrrole rings = 2.3 (3)°] and two tetramethylene substituents at the 2,3- and 5,6-positions in a half-chair conformation. One of the tetramethylene substituents is disordered over two two sets of sites with site occupancies of 0.5. In the crystal, pairs of C—H...F interactions link the molecules into inversion dimers. Neighbouring dimers are linked by further C—H...F interactions, forming an infinite array. C—H...π and π–π [centroid–centroid distance = 4.360 (3) Å] interac…
One-pot synthesis and characterization of subnanometre-size benzotriazolate protected copper clusters
A simple one-pot method for the preparation of subnanometre-size benzotriazolate (BTA) protected copper clusters, Cu(n)BTA(m), is reported. The clusters were analyzed by optical and infrared spectroscopy, mass spectrometry and transmission electron microscopy together with computational methods. We suggest a structural motif where the copper core of the Cu(n)BTA(m) clusters is protected by BTA-Cu(i)-BTA units.
Vibrational Perturbations and Ligand–Layer Coupling in a Single Crystal of Au144(SC2H4Ph)60 Nanocluster
We have determined vibrational signatures and optical gap of the Au144(PET)60 (PET: phenylethylthiol, SC2H4Ph) nanocluster solvated in deuterated dichloromethane (DCM-D2, CD2Cl2) and in a single crystal. For crystals, solid-state (13)C NMR and X-ray diffraction were also measured. A revised value of 2200 cm(-1) (0.27 eV) was obtained for the optical gap in both phases. The vibrational spectra of solvated AU144(PET)60 closely resembles that of neat PET, while the crystalline-state spectrum exhibits significant inhomogeneous spectral broadening, frequency shifts, intensity transfer between vibrational modes, and an increase in the overtone and combination transition intensities. Spectral broa…
Exploring the atomic structure of 1.8 nm monolayer-protected gold clusters with aberration-corrected STEM
Abstract Monolayer-protected (MP) Au clusters present attractive quantum systems with a range of potential applications e.g. in catalysis. Knowledge of the atomic structure is needed to obtain a full understanding of their intriguing physical and chemical properties. Here we employed aberration-corrected scanning transmission electron microscopy (ac-STEM), combined with multislice simulations, to make a round-robin investigation of the atomic structure of chemically synthesised clusters with nominal composition Au 144 (SCH 2 CH 2 Ph) 60 provided by two different research groups. The MP Au clusters were “weighed” by the atom counting method, based on their integrated intensities in the high …
Jahn–Teller effects in Au25(SR)18
The relationship between oxidation state, structure, and magnetism in many molecules is well described by first-order Jahn–Teller distortions. This relationship is not yet well defined for ligated nanoclusters and nanoparticles, especially the nano-technologically relevant gold-thiolate protected metal clusters. Here we interrogate the relationships between structure, magnetism, and oxidation state for the three stable oxidation states, 1, 0 and +1 of the thiolate protected nanocluster Au25(SR)18. We present the single crystal X-ray structures of the previously undetermined charge state Au25(SR)18+1, as well as a higher quality single crystal structure of the neutral compound Au25(SR)180 . …
CCDC 919270: Experimental Crystal Structure Determination
Related Article: Tiia-Riikka Tero, Aku Suhonen, Kirsi Salorinne, Hélène Campos-Barbosa, Maija Nissinen|2013|Org.Lett.|15|1096|doi:10.1021/ol400118t
CCDC 1044958: Experimental Crystal Structure Determination
Related Article: Tiia-Riikka Tero, Kirsi Salorinne, Sami Malola, Hannu Häkkinen, Maija Nissinen|2015|CrystEngComm|17|8231|doi:10.1039/C5CE01144B
CCDC 999257: Experimental Crystal Structure Determination
Related Article: Kirsi Salorinne, Tanja Lahtinen, Varpu Marjomäki, Hannu Häkkinen|2014|CrystEngComm|16|9001|doi:10.1039/C4CE01152J
CCDC 999254: Experimental Crystal Structure Determination
Related Article: Kirsi Salorinne, Tanja Lahtinen, Varpu Marjomäki, Hannu Häkkinen|2014|CrystEngComm|16|9001|doi:10.1039/C4CE01152J
CCDC 1482405: Experimental Crystal Structure Determination
Related Article: Ville K. Saarnio, Kirsi Salorinne, Visa P. Ruokolainen, Jesper R. Nilsson, Tiia-Riikka Tero, Sami Oikarinen, L. Marcus Wilhelmsson, Tanja M. Lahtinen, Varpu S. Marjomäki|2020|Dyes Pigm.|177|108282|doi:10.1016/j.dyepig.2020.108282
CCDC 943017: Experimental Crystal Structure Determination
Related Article: Tiia-Riikka Tero, Kirsi Salorinne, Heli Lehtivuori, Janne A. Ihalainen, Maija Nissinen|2014|Chem.Asian J.|9|1860|doi:10.1002/asia.201402016
CCDC 943016: Experimental Crystal Structure Determination
Related Article: Tiia-Riikka Tero, Kirsi Salorinne, Heli Lehtivuori, Janne A. Ihalainen, Maija Nissinen|2014|Chem.Asian J.|9|1860|doi:10.1002/asia.201402016
CCDC 943015: Experimental Crystal Structure Determination
Related Article: Tiia-Riikka Tero, Kirsi Salorinne, Heli Lehtivuori, Janne A. Ihalainen, Maija Nissinen|2014|Chem.Asian J.|9|1860|doi:10.1002/asia.201402016
CCDC 1055143: Experimental Crystal Structure Determination
Related Article: Marcus A. Tofanelli, Kirsi Salorinne, Thomas W. Ni, Sami Malola, Brian Newell, Billy Phillips, Hannu Häkkinen, Christopher J. Ackerson|2016|Chemical Science|7|1882|doi:10.1039/C5SC02134K
CCDC 919269: Experimental Crystal Structure Determination
Related Article: Tiia-Riikka Tero, Aku Suhonen, Kirsi Salorinne, Hélène Campos-Barbosa, Maija Nissinen|2013|Org.Lett.|15|1096|doi:10.1021/ol400118t
CCDC 919268: Experimental Crystal Structure Determination
Related Article: Tiia-Riikka Tero, Aku Suhonen, Kirsi Salorinne, Hélène Campos-Barbosa, Maija Nissinen|2013|Org.Lett.|15|1096|doi:10.1021/ol400118t
CCDC 1044955: Experimental Crystal Structure Determination
Related Article: Tiia-Riikka Tero, Kirsi Salorinne, Sami Malola, Hannu Häkkinen, Maija Nissinen|2015|CrystEngComm|17|8231|doi:10.1039/C5CE01144B
CCDC 1985367: Experimental Crystal Structure Determination
Related Article: Kirsi Salorinne, Renee W. Y. Man, Paul A. Lummis, Maryam Sabooni Asre Hazer, Sami Malola, Jacky C.-H. Yim, Alex J. Veinot, Wenxia Zhou, Hannu Häkkinen, Masakazu Nambo, Cathleen M. Crudden|2020|Chem.Commun.|56|6102|doi:10.1039/D0CC01482F
CCDC 1482404: Experimental Crystal Structure Determination
Related Article: Ville K. Saarnio, Kirsi Salorinne, Visa P. Ruokolainen, Jesper R. Nilsson, Tiia-Riikka Tero, Sami Oikarinen, L. Marcus Wilhelmsson, Tanja M. Lahtinen, Varpu S. Marjomäki|2020|Dyes Pigm.|177|108282|doi:10.1016/j.dyepig.2020.108282
CCDC 919271: Experimental Crystal Structure Determination
Related Article: Tiia-Riikka Tero, Aku Suhonen, Kirsi Salorinne, Hélène Campos-Barbosa, Maija Nissinen|2013|Org.Lett.|15|1096|doi:10.1021/ol400118t
CCDC 1044957: Experimental Crystal Structure Determination
Related Article: Tiia-Riikka Tero, Kirsi Salorinne, Sami Malola, Hannu Häkkinen, Maija Nissinen|2015|CrystEngComm|17|8231|doi:10.1039/C5CE01144B
CCDC 1055144: Experimental Crystal Structure Determination
Related Article: Marcus A. Tofanelli, Kirsi Salorinne, Thomas W. Ni, Sami Malola, Brian Newell, Billy Phillips, Hannu Häkkinen, Christopher J. Ackerson|2016|Chemical Science|7|1882|doi:10.1039/C5SC02134K
CCDC 1985364: Experimental Crystal Structure Determination
Related Article: Kirsi Salorinne, Renee W. Y. Man, Paul A. Lummis, Maryam Sabooni Asre Hazer, Sami Malola, Jacky C.-H. Yim, Alex J. Veinot, Wenxia Zhou, Hannu Häkkinen, Masakazu Nambo, Cathleen M. Crudden|2020|Chem.Commun.|56|6102|doi:10.1039/D0CC01482F
CCDC 1044956: Experimental Crystal Structure Determination
Related Article: Tiia-Riikka Tero, Kirsi Salorinne, Sami Malola, Hannu Häkkinen, Maija Nissinen|2015|CrystEngComm|17|8231|doi:10.1039/C5CE01144B
CCDC 1044959: Experimental Crystal Structure Determination
Related Article: Tiia-Riikka Tero, Kirsi Salorinne, Sami Malola, Hannu Häkkinen, Maija Nissinen|2015|CrystEngComm|17|8231|doi:10.1039/C5CE01144B
CCDC 1044954: Experimental Crystal Structure Determination
Related Article: Tiia-Riikka Tero, Kirsi Salorinne, Sami Malola, Hannu Häkkinen, Maija Nissinen|2015|CrystEngComm|17|8231|doi:10.1039/C5CE01144B
CCDC 999255: Experimental Crystal Structure Determination
Related Article: Kirsi Salorinne, Tanja Lahtinen, Varpu Marjomäki, Hannu Häkkinen|2014|CrystEngComm|16|9001|doi:10.1039/C4CE01152J
CCDC 943014: Experimental Crystal Structure Determination
Related Article: Tiia-Riikka Tero, Kirsi Salorinne, Heli Lehtivuori, Janne A. Ihalainen, Maija Nissinen|2014|Chem.Asian J.|9|1860|doi:10.1002/asia.201402016
CCDC 999256: Experimental Crystal Structure Determination
Related Article: Kirsi Salorinne, Tanja Lahtinen, Varpu Marjomäki, Hannu Häkkinen|2014|CrystEngComm|16|9001|doi:10.1039/C4CE01152J