0000000000845528
AUTHOR
Liu-pan Yang
A conformationally adaptive macrocycle : conformational complexity and host–guest chemistry of zorb[4]arene
Large amplitude conformational change is one of the features of biomolecular recognition and is also the basis for allosteric effects and signal transduction in functional biological systems. However, synthetic receptors with controllable conformational changes are rare. In this article, we present a thorough study on the host–guest chemistry of a conformationally adaptive macrocycle, namely per-O-ethoxyzorb[4]arene (ZB4). Similar to per-O-ethoxyoxatub[4]arene, ZB4 is capable of accommodating a wide range of organic cations. However, ZB4 does not show large amplitude conformational responses to the electronic substituents on the guests. Instead of a linear free-energy relationship, ZB4 foll…
Probing the guest-binding preference of three structurally similar and conformationally adaptive macrocycles.
A hybrid macrocycle was synthesized by combining the repeat units in oxatub[4]arene and zorb[4]arene, and its recognition behavior and conformational analysis were studied. Three structurally similar and conformationally adaptive macrocycles show different guest-binding selectivities and preferences even in a complex mixture containing three macrocycles and three guests.
Effects of side chains of oxatub[4]arene on its conformational interconversion, molecular recognition and macroscopic self-assembly.
A series of oxatub[4]arenes with different alkyl side chains have been synthesized. The conformational interconversion, molecular recognition and macroscopic self-assembly behaviour of oxatub[4]arene derivatives were investigated. The difference in side chains slightly changes the binding affinities, but results in different self-assembly morphologies at the solid state.
A supramolecular system that strictly follows the binding mechanism of conformational selection
Induced fit and conformational selection are two dominant binding mechanisms in biology. Although induced fit has been widely accepted by supramolecular chemists, conformational selection is rarely studied with synthetic systems. In the present research, we report a macrocyclic host whose binding mechanism is unambiguously assigned to conformational selection. The kinetic and thermodynamic aspects of this system are studied in great detail. It reveals that the kinetic equation commonly used for conformational selection is strictly followed here. In addition, two mathematical models are developed to determine the association constants of the same guest to the two host conformations. A “confo…
Redox-Responsive Host-Guest Chemistry of a Flexible Cage with Naphthalene Walls
“Naphthocage”, a naphthalene-based organic cage, reveals very strong binding (up to 1010 M–1) to aromatic (di)cationic guests, i.e., the tetrathiafulvalene mono- and dication and methyl viologen. Intercalation of the guests between two naphthalene walls is mediated by C–H···O, C–H···π, and cation···π interactions. The guests can be switched into and out of the cage by redox processes with high binding selectivity. Oxidation of the flexible cage itself in the absence of a guest leads to a stable radical cation with the oxidized naphthalene intercalated between and stabilized by the other two. Encapsulated guest cations are released from the cavity upon cage oxidation, paving the way to futur…
Redox-Responsive Host–Guest Chemistry of a Flexible Cage with Naphthalene Walls
"Naphthocage", a naphthalene-based organic cage, reveals very strong binding (up to 1010 M-1) to aromatic (di)cationic guests, i.e., the tetrathiafulvalene mono- and dication and methyl viologen. Intercalation of the guests between two naphthalene walls is mediated by C-H···O, C-H···π, and cation···π interactions. The guests can be switched into and out of the cage by redox processes with high binding selectivity. Oxidation of the flexible cage itself in the absence of a guest leads to a stable radical cation with the oxidized naphthalene intercalated between and stabilized by the other two. Encapsulated guest cations are released from the cavity upon cage oxidation, paving the way to futur…
A 2,3-dialkoxynaphthalene-based naphthocage
A 2,3-dialkoxynaphthalene-based naphthocage has been synthesized. This naphthocage prefers to bind small organic cations with its low-symmetry conformation, which is in contrast to 2,6-dialkoxynaphthalene-based naphthocages. Self-sorting of these two naphthocages with two structurally similar guests tetramethylammonium and tetraethylammonium was achieved as well. peerReviewed
Guest-Induced Folding and Self-Assembly of Conformationally Adaptive Macrocycles into Nanosheets and Nanotubes
A conformationally adaptive macrocycle is presented, namely zorb[4]arene, which exists in multiple conformations in the uncomplexed state. The binding cavity of zorb[4]arene is concealed, either due to a collapsed conformation or by self-inclusion. The zorb[4]arene with long alkyl chains manifests itself with surprisingly low melting point and thus exist as an oil at room temperature. Binding of a guest molecule induces the folding and conformational rigidity of zorb[4]arene and leads to well-defined three-dimensional structures, which can further self-assemble into nanosheets or nanotubes upon solvent evaporation, depending on guest molecules and the conformations they can induce.
CCDC 1913149: Experimental Crystal Structure Determination
Related Article: Hongxin Chai, Zhi-Sheng Pan, Liu-Pan Yang, Shan He, Fangfang Pan, Kari Rissanen, Wei Jiang|2019|Chem.Commun.|55|7768|doi:10.1039/C9CC03341F
CCDC 1577176: Experimental Crystal Structure Determination
Related Article: Liu-Pan Yang, Fei Jia, Fangfang Pan, Zhi-Sheng Pan, Kari Rissanen, Wei Jiang|2017|Chem.Commun.|53|12572|doi:10.1039/C7CC07630D
A conformationally adaptive macrocycle: conformational complexity and host–guest chemistry of zorb[4]arene
Large amplitude conformational change is one of the features of biomolecular recognition and is also the basis for allosteric effects and signal transduction in functional biological systems. However, synthetic receptors with controllable conformational changes are rare. In this article, we present a thorough study on the host–guest chemistry of a conformationally adaptive macrocycle, namely per-O-ethoxyzorb[4]arene (ZB4). Similar to per-O-ethoxyoxatub[4]arene, ZB4 is capable of accommodating a wide range of organic cations. However, ZB4 does not show large amplitude conformational responses to the electronic substituents on the guests. Instead of a linear free-energy relationship, ZB4 foll…
CCDC 1957981: Experimental Crystal Structure Determination
Related Article: Fei Jia, Hendrik V. Schröder, Liu-Pan Yang, Carolina von Essen, Sebastian Sobottka, Biprajit Sarkar, Kari Rissanen, Wei Jiang, Christoph A. Schalley|2020|J.Am.Chem.Soc.|142|3306|doi:10.1021/jacs.9b11685
CCDC 1838266: Experimental Crystal Structure Determination
Related Article: Liu-Pan Yang, Song-Bo Lu, Arto Valkonen, Fangfang Pan, Kari Rissanen, Wei Jiang|2018|Beilstein J.Org.Chem.|14|1570|doi:10.3762/bjoc.14.134
CCDC 1913150: Experimental Crystal Structure Determination
Related Article: Hongxin Chai, Zhi-Sheng Pan, Liu-Pan Yang, Shan He, Fangfang Pan, Kari Rissanen, Wei Jiang|2019|Chem.Commun.|55|7768|doi:10.1039/C9CC03341F
CCDC 1950443: Experimental Crystal Structure Determination
Related Article: Liu-Pan Yang, Li Zhang, Mao Quan, Jas S. Ward, Yan-Long Ma, Hang Zhou, Kari Rissanen, Wei Jiang|2020|Nat.Commun.|11|2740|doi:10.1038/s41467-020-16534-9
CCDC 1836247: Experimental Crystal Structure Determination
Related Article: Liu-Pan Yang, Song-Bo Lu, Arto Valkonen, Fangfang Pan, Kari Rissanen, Wei Jiang|2018|Beilstein J.Org.Chem.|14|1570|doi:10.3762/bjoc.14.134
CCDC 1836509: Experimental Crystal Structure Determination
Related Article: Liu-Pan Yang, Song-Bo Lu, Arto Valkonen, Fangfang Pan, Kari Rissanen, Wei Jiang|2018|Beilstein J.Org.Chem.|14|1570|doi:10.3762/bjoc.14.134
CCDC 1482002: Experimental Crystal Structure Determination
Related Article: Liu-Pan Yang, Fei Jia, Qing-Hai Zhou, Fangfang Pan, Jiao-Nan Sun, Kari Rissanen, Lung Wa Chung, Wei Jiang|2017|Chem.-Eur.J.|23|1516|doi:10.1002/chem.201605701
CCDC 1838268: Experimental Crystal Structure Determination
Related Article: Liu-Pan Yang, Song-Bo Lu, Arto Valkonen, Fangfang Pan, Kari Rissanen, Wei Jiang|2018|Beilstein J.Org.Chem.|14|1570|doi:10.3762/bjoc.14.134
CCDC 1482001: Experimental Crystal Structure Determination
Related Article: Liu-Pan Yang, Fei Jia, Qing-Hai Zhou, Fangfang Pan, Jiao-Nan Sun, Kari Rissanen, Lung Wa Chung, Wei Jiang|2017|Chem.-Eur.J.|23|1516|doi:10.1002/chem.201605701
CCDC 1971100: Experimental Crystal Structure Determination
Related Article: Song-Bo Lu, Hongxin Chai, Jas S. Ward, Mao Quan, Jin Zhang, Kari Rissanen, Ray Luo, Liu-Pan Yang, Wei Jiang|2020|Chem.Commun.|56|888|doi:10.1039/C9CC09585C
CCDC 1838267: Experimental Crystal Structure Determination
Related Article: Liu-Pan Yang, Song-Bo Lu, Arto Valkonen, Fangfang Pan, Kari Rissanen, Wei Jiang|2018|Beilstein J.Org.Chem.|14|1570|doi:10.3762/bjoc.14.134
CCDC 1838270: Experimental Crystal Structure Determination
Related Article: Liu-Pan Yang, Song-Bo Lu, Arto Valkonen, Fangfang Pan, Kari Rissanen, Wei Jiang|2018|Beilstein J.Org.Chem.|14|1570|doi:10.3762/bjoc.14.134
CCDC 1913148: Experimental Crystal Structure Determination
Related Article: Hongxin Chai, Zhi-Sheng Pan, Liu-Pan Yang, Shan He, Fangfang Pan, Kari Rissanen, Wei Jiang|2019|Chem.Commun.|55|7768|doi:10.1039/C9CC03341F
CCDC 1838269: Experimental Crystal Structure Determination
Related Article: Liu-Pan Yang, Song-Bo Lu, Arto Valkonen, Fangfang Pan, Kari Rissanen, Wei Jiang|2018|Beilstein J.Org.Chem.|14|1570|doi:10.3762/bjoc.14.134