Synthesis, enantiomeric resolution and photophysical properties of 7-cyano-14-methoxy-5-thiahexahelicene

被引:6
作者
Hafedh, Nesrine [1 ]
Aloui, Faouzi [1 ]
Raouafi, Sondes [1 ]
机构
[1] Univ Monastir, Fac Sci, Lab Asymetr Organ Synth & Homogenous Catalysis, UR11ES56, Ave Environm, Monastir 5019, Tunisia
关键词
Chirality; Helicenes; Photolysis; Enantiomeric resolution; Photophysical properties; CIRCULARLY-POLARIZED LUMINESCENCE; ONE HUNDRED YEARS; NONLINEAR-OPTICAL PROPERTIES; CHIROPTICAL PROPERTIES; CHIRAL RECOGNITION; STEREOSELECTIVE SYNTHESES; ELECTRONIC-PROPERTIES; ASYMMETRIC CATALYSIS; HELICENES; MOLECULES;
D O I
10.1016/j.molstruc.2018.03.067
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A simple and efficient approach leading to a well functionalized helically chiral pi-conjugated system is reported. Optical resolution of racemic helicene has been well accomplished affording both enantiomers (+)- and (-)-4 in high optical purity and their chiroptical properties were experimentally evaluated. Based on electronic circular dichroism (ECD) absolute configurations of dextrorotary and laevorotatory antipodes were assigned as P and M, respectively. Photophysical properties of the helical compound have been also examined in solutions and show a remarkable behaviour. (C) 2018 Elsevier B.V. All rights reserved.
引用
收藏
页码:126 / 131
页数:6
相关论文
共 78 条
[1]   Helicene-like chiral auxiliaries in asymmetric catalysis [J].
Aillard, P. ;
Voituriez, A. ;
Marinetti, A. .
DALTON TRANSACTIONS, 2014, 43 (41) :15263-15278
[2]   Synthesis and resolution of a new helically chiral azahelicene [J].
Aloui, Faouzi ;
El Abed, Riadh ;
Marinetti, Angla ;
Ben Hassine, Bechir .
TETRAHEDRON LETTERS, 2008, 49 (26) :4092-4095
[3]   Chiral recognition in noncovalent bonding interactions between helicenes: right-handed helix favors right-handed helix over left-handed helix [J].
Amemiya, Ryo ;
Yamaguchi, Masahiko .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (01) :26-35
[4]  
[Anonymous], 1974, ANGEW CHEM, V86, P727, DOI DOI 10.1002/ANGE.19740862003
[5]   Synthesis, enantiomeric resolution and optical properties of 8-cyanohexahelicene [J].
Ben Braiek, Mourad ;
Aloui, Faouzi ;
Ben Hassine, Bechir .
TETRAHEDRON LETTERS, 2016, 57 (38) :4273-4276
[6]  
BENHASSINE B, 1986, B SOC CHIM BELG, V95, P547
[7]   Physicochemical and Electronic Properties of Cationic [6]Helicenes: from Chemical and Electrochemical Stabilities to Far-Red (Polarized) Luminescence [J].
Bosson, Johann ;
Labrador, Geraldine M. ;
Pascal, Simon ;
Miannay, Francois-Alexandre ;
Yushchenko, Oleksandr ;
Li, Haidong ;
Bouffier, Laurent ;
Sojic, Neso ;
Tovar, Roberto C. ;
Muller, Gilles ;
Jacquemin, Denis ;
Laurent, Adele D. ;
Le Guennic, Boris ;
Vauthey, Eric ;
Lacour, Jerome .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (51) :18394-18403
[8]   Thieno[3,2-b]thiophene-Diketopyrrolopyrrole-Containing Polymers for High-Performance Organic Field-Effect Transistors and Organic Photovoltaic Devices [J].
Bronstein, Hugo ;
Chen, Zhuoying ;
Ashraf, Rap Shahid ;
Zhang, Weimin ;
Du, Junping ;
Durrant, James R. ;
Tuladhar, Pabitra Shakya ;
Song, Kigook ;
Watkins, Scott E. ;
Geerts, Yves ;
Wienk, Martijn M. ;
Janssen, Rene A. J. ;
Anthopoulos, Thomas ;
Sirringhaus, Henning ;
Heeney, Martin ;
McCulloch, Iain .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (10) :3272-3275
[9]   Synthesis, Functionalization, and Optical Properties of Chiral Carbazole-Based Diaza[6]helicenes [J].
Bucinskas, Audrius ;
Waghray, Deepali ;
Bagdziunas, Gintautas ;
Thomas, Joice ;
Grazulevicius, Juozas Vidas ;
Dehaen, Wim .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (05) :2521-2528
[10]   Synthesis and properties of a thiophene-substituted diaza[7]helicene for application as a blue emitter in organic light-emitting diodes [J].
Chen, Ting ;
Zhang, Baojie ;
Liu, Zhi ;
Duan, Lian ;
Dong, Guifang ;
Feng, Ying ;
Luo, Xinyu ;
Cui, Deliang .
TETRAHEDRON LETTERS, 2017, 58 (06) :531-535