Enantioselective synthesis of helical polydiacetylenes in the visible light region.

Herein, we demonstrate for the first time that the enantio-selective polymerization of DA monomers could be realized upon irradiation with circularly polarized visible light (CPVL), which could effectively provide chiral order in the propagating step of a polymerization reaction.

[1]  Keyi Wang,et al.  Control of supramolecular chirality for polydiacetylene LB films with the command azobenzene derivative monolayer , 2011 .

[2]  Hao Jiang,et al.  Chiroptical switch based on azobenzene-substituted polydiacetylene LB films under thermal and photic stimuli , 2010 .

[3]  K. Akagi,et al.  Helically π-Stacked Thiophene-Based Copolymers with Circularly Polarized Fluorescence: High Dissymmetry Factors Enhanced by Self-Ordering in Chiral Nematic Liquid Crystal Phase , 2012 .

[4]  M. C. Stuart,et al.  Topochemical polymerization of naphthalenediimide-substituted diacetylene suspensions , 2002 .

[5]  Satoshi Matsushita,et al.  Lyotropic chiral nematic liquid crystalline aliphatic conjugated polymers based on disubstituted polyacetylene derivatives that exhibit high dissymmetry factors in circularly polarized luminescence. , 2012, Journal of the American Chemical Society.

[6]  Gang Zou,et al.  Ruthenium(II) complex-sensitized solid-state polymerization of diacetylene in the visible light region , 2008 .

[7]  C. Bubeck,et al.  Sensitized photoreaction of diacetylene multilayers , 1983 .

[8]  Hao Jiang,et al.  Control and modulation of chirality for azobenzene-substituted polydiacetylene LB films with circularly polarized light. , 2009, Chemical communications.

[9]  L. Liu,et al.  Acidichromism and Supramolecular Chirality of Tetrakis(4-sulfonatophenyl)porphyrin in Organized Molecular Films , 2008 .

[10]  Kovuru Gopalaiah,et al.  Chiral iron catalysts for asymmetric synthesis. , 2013, Chemical reviews.

[11]  K. Ishikawa,et al.  A general method for the enantioselective formation of helical nanofilaments. , 2013, Angewandte Chemie.

[12]  G. Schuster,et al.  Photoresolution of an Axially Chiral Bicyclo[3.2.1]octan-3-one: Phototriggers for a Liquid Crystal-Based Optical Switch , 1995 .

[13]  S. Pizzarello,et al.  Enantiomeric Excesses in Meteoritic Amino Acids , 1997, Science.

[14]  G. Wegner,et al.  Mechanisms of the Spectral Sensitization of the Diacetylene Polymerization , 1983 .

[15]  L. Samuelson,et al.  Nanocrystalline TiO2-catalyzed solid-state polymerization of diacetylene in the visible region. , 2007, Journal of the American Chemical Society.

[16]  J. Hough,et al.  Circular polarization in star-formation regions: implications for biomolecular homochirality. , 1998, Science.

[17]  M. Liu,et al.  Chirality of photopolymerized organized supramolecular polydiacetylene films. , 2003, Chemical communications.

[18]  W. Bonner,et al.  Asymmetric photolysis of (RS)-leucine with circularly polarized ultraviolet light. , 1977, Journal of the American Chemical Society.

[19]  Xunhua Liu,et al.  A tetraphenylethene-based chiral polymer: an AIE luminogen with high and tunable CPL dissymmetry factor , 2013 .

[20]  Yoshihisa Inoue.  Asymmetric photochemical reactions in solution , 1992 .

[21]  Takaaki Manaka,et al.  Preparation of Chiral Polydiacetylene Film from Achiral Monomers Using Circularly Polarized Light , 2006 .

[22]  Asymmetric photochemistry and photochirogenesis. , 2002, Angewandte Chemie.

[23]  Huisheng Peng,et al.  Chromatic polydiacetylene with novel sensitivity. , 2010, Chemical Society reviews.

[24]  I. Weissbuch,et al.  Crystalline architectures as templates of relevance to the origins of homochirality. , 2011, Chemical reviews.

[25]  G. Bolbach,et al.  Racemic β sheets in biochirogenesis , 2007 .

[26]  H. Pingsheng,et al.  Polymerization kinetics of 10,12-pentacosadiynoic acid monolayer and possible acceleration effect of visible light , 2003 .

[27]  Theo Rasing,et al.  Complete chiral symmetry breaking of an amino acid derivative directed by circularly polarized light. , 2009, Nature chemistry.

[28]  B. A. Pindzola,et al.  Biosensing with polydiacetylene materials: structures, optical properties and applications. , 2007, Chemical communications.

[29]  Ben L. Feringa,et al.  Dynamic Control and Amplification of Molecular Chirality by Circular Polarized Light , 1996, Science.

[30]  Jong-Man Kim,et al.  Recent conceptual and technological advances in polydiacetylene-based supramolecular chemosensors. , 2009, Chemical Society reviews.