Band Gap of Carbon-Sulfur [n]Helicenes

被引:33
作者
Miyasaka, Makoto [1 ]
Pink, Maren [2 ]
Olankitwanit, Arnon [1 ]
Rajca, Suchada [1 ]
Rajca, Andrzej [1 ]
机构
[1] Univ Nebraska, Dept Chem, Lincoln, NE 68588 USA
[2] Indiana Univ, Dept Chem, IUMSC, Bloomington, IN 47405 USA
基金
美国国家科学基金会;
关键词
CROSS-CONJUGATED OLIGOTHIOPHENES; ASYMMETRIC-SYNTHESIS; RESOLUTION;
D O I
10.1021/ol3011437
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric synthesis of (-)-[9]helicene, as well as preparation of its lower homologues, completes the series of carbon-sulfur [5]-, [7]-, [9]-, and [11]helicenes. Spectroscopic and electrochemical studies of this series provide an absorption onset-based band gap, E-g = 3.40 eV, for a cross-conjugated (C2S)(n) helix; this value may be compared to E-g = 3.59 eV obtained from TD-DFT computed excitation energies for a series of dimethyl-substituted [n]helicenes (n <= 31).
引用
收藏
页码:3076 / 3079
页数:4
相关论文
共 36 条
[21]  
Rajca A, 2000, ANGEW CHEM INT EDIT, V39, P4481, DOI 10.1002/1521-3773(20001215)39:24<4481::AID-ANIE4481>3.0.CO
[22]  
2-G
[23]   A Greek cross dodecaphenylene:: sparteine-mediated asymmetric synthesis of chiral D2-symmetric π-conjugated tetra-o-phenylenes [J].
Rajca, A ;
Wang, H ;
Bolshov, P ;
Rajca, S .
TETRAHEDRON, 2001, 57 (17) :3725-3735
[24]   D2-symmetric dimer of 1,1′-binaphthyl and its chiral π-conjugated carbodianion [J].
Rajca, A ;
Safronov, A ;
Rajca, S ;
Wongsriratanakul, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (14) :3351-3357
[25]  
Rajca A., 2007, Functional Organic Materials, P543, DOI DOI 10.1002/9783527610266.CH15
[26]   Annelated, chiral π-conjugated systems:: Tetraphenylenes and helical β-oligothiophenes [J].
Rajca, Andrzej ;
Rajca, Suchada ;
Pink, Maren ;
Miyasaka, Makoto .
SYNLETT, 2007, (12) :1799-1822
[27]   Ladder Oligo(m-aniline)s: Derivatives of Azaacenes with Cross-Conjugated π-Systems [J].
Rajca, Andrzej ;
Boratynski, Przemyslaw J. ;
Olankitwanit, Arnon ;
Shiraishi, Kouichi ;
Pink, Maren ;
Rajca, Suchada .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (05) :2107-2120
[28]   Asymmetric Synthesis of Chiral Tetraphenylenes [J].
Rajca, Andrzej ;
Rajca, Suchada .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (04) :672-674
[29]   Functionalized Thiophene-Based [7]Helicene: Chirooptical Properties versus Electron Delocalization [J].
Rajca, Andrzej ;
Pink, Maren ;
Xiao, Shuzhang ;
Miyasaka, Makoto ;
Rajca, Suchada ;
Das, Kausik ;
Plessel, Kristin .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (19) :7504-7513
[30]   A quantum-chemical perspective into low optical-gap polymers for highly-efficient organic solar cells [J].
Risko, Chad ;
McGehee, Michael D. ;
Bredas, Jean-Luc .
CHEMICAL SCIENCE, 2011, 2 (07) :1200-1218