Towards sensory Langmuir monolayers consisting of macrocyclic pentaaminoanthraquinone

A pentaazamacrocycle incorporating an intracyclic anthraquinone fragment (PENTAQ) was synthesized with the aim of forming metal-responsive Langmuir monolayers. PENTAQ allows a good discrimination by naked eye of copper ions in methanol–water solutions (50 : 50 v/v). Spectrophotometric investigations of the protonation and Cu2+ binding properties of PENTAQ were undertaken in order to gain a deeper insight into the pH-dependent speciation as well as the color changing process. PENTAQ monolayers at air/water and air/methanol–water interfaces were prepared according to the Langmuir procedure. The structure of the monolayers can be tuned by varying the pH of the aqueous subphase, since it was fo…

Synthesis of (trans-A2)BC-Type Porphyrins with Acceptor Diethoxyphosphoryl and Various Donor Groups and their Assembling in the Solid State and at Interfaces

Design and evaluation of sensory systems based on amphiphilic anthraquinones molecular receptors

A new paradigm is described that allows one to create different types of sensors: from highly sensitive ones to practical household devices. Our approach relies on modular molecular receptors incorporating an intensely-colored aminoanthraquinone signaling unit equipped with both hydrophilic and hydrophobic modules, the number and size of which being configured in accordance with the targeted analyte and the sought detection method. An important advantage is the compliance with some principles of green chemistry, avoiding the use of toxic organic solvents. The proper functionalization of the anthraquinone scaffold afforded water-soluble chromoinophores capable of quantifying selectively Hg2+…

A metal-responsive interdigitated bilayer for selective quantification of mercury( ii ) traces by surface plasmon resonance

Reusable surface plasmon resonance chips allowing the quantitative and selective detection of mercury(II) ions in water at the 0.01 nM level are reported. The surface-modified gold sensor consists of a rarefied self-assembled monolayer of octanethiol topped with a Langmuir–Blodgett monolayer of an amphiphilic and highly-specific chelator. The interdigitated architecture confers to the bilayer a high packing density, surface coverage, and binding-group accessibility.

Ultra-thin film sensors based on porphyrin-5-ylphosphonate diesters for selective and sensitive dual-channel optical detection of mercury(II) ions

International audience; Reusable dual-channel optical sensors for Hg2+ ions were prepared by Langmuir-Schaefer (LS) method from amphiphilic (trans-A2)BC-type porphyrins functionalized at meso-positions of the tetrapyrrolic macrocycle by sterically demanding diethoxyphosphoryl and mesityl groups as well as electron donating RO, RS or RNH substituents (R = n-C8H17). These three novel amphiphilic porphyrin derivatives were synthesized in good yields and their floating films at the air⎯water interface were investigated. In these monolayers, porphyrin molecules display a slipped stack-of-card orientation, but their strong π stacking is prohibited by bulky diethoxyphosphoryl and mesityl groups. T…

CCDC 945040: Experimental Crystal Structure Determination

Related Article: Elena Ranyuk, Elizaveta V. Ermakova, Laura Bovigny, Michel Meyer, Alla Bessmertnykh-Lemeune, Roger Guilard, Yoann Rousselin, Aslan Yu. Tsivadze, Vladimir V. Arslanov|2014|New J.Chem.|38|317|doi:10.1039/C3NJ01121F

CCDC 1893716: Experimental Crystal Structure Determination

Related Article: Elizaveta V. Ermakova, Yulia Y. Enakieva, Sergey E. Nefedov, Vladimir V. Arslanov, Yulia G. Gorbunova, Aslan Y. Tsivadze, Christine Stern, Alla Lemeune|2019|Eur.J.Org.Chem.|2019|3146|doi:10.1002/ejoc.201900448

CCDC 945039: Experimental Crystal Structure Determination

Related Article: Elena Ranyuk, Elizaveta V. Ermakova, Laura Bovigny, Michel Meyer, Alla Bessmertnykh-Lemeune, Roger Guilard, Yoann Rousselin, Aslan Yu. Tsivadze, Vladimir V. Arslanov|2014|New J.Chem.|38|317|doi:10.1039/C3NJ01121F