Photophysical property trends for a homologous series of bis-ethynyl-substituted benzochalcogendiazoles

被引:29
作者
Coombs, Benjamin A. [2 ]
Lindner, Benjamin D. [2 ]
Edkins, Robert M. [1 ]
Rominger, Frank [2 ]
Beeby, Andrew [1 ]
Bunz, Uwe H. F. [2 ]
机构
[1] Durham Univ Sci Site, Dept Chem, Durham DH1 3LE, England
[2] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany
关键词
OPTOELECTRONIC PROPERTIES; DERIVATIVES; SULFUR; POLYMERS; OXYGEN;
D O I
10.1039/c2nj20847d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report on the preparation and photophysical property study of three homologous benzoheteroarene-ethynylene systems. Significant differences in the series' optical properties indicate a change in the HOMO-LUMO energy as the chalcogen is altered (O, S and Se) which we have examined using TD-DFT methods and shown to be attributable to modification of the HOMO energy.
引用
收藏
页码:550 / 553
页数:4
相关论文
共 30 条
[1]   Synthesis and characterization of new linear π-conjugated molecules containing bis(ethynylpyridine) units with a benzothiadiazole spacer [J].
Akhtaruzzaman, M ;
Tomura, M ;
Zaman, MB ;
Nishida, J ;
Yamashita, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (22) :7813-7818
[2]  
[Anonymous], SPART 10
[3]  
Appleton A. L., 2010, COMMUN, V1, P1
[4]   Alkynylated Aceno[2,1,3]thiadiazoles [J].
Appleton, Anthony Lucas ;
Miao, Shaobin ;
Brombosz, Scott M. ;
Berger, Nancy J. ;
Barlow, Stephen ;
Marder, Seth R. ;
Lawrence, Brian M. ;
Hardcastle, Kenneth I. ;
Bunz, Uwe H. F. .
ORGANIC LETTERS, 2009, 11 (22) :5222-5225
[5]   Attachment of an electron-withdrawing fluorophore to a cryptand for modulation of fluorescence signaling [J].
Bag, B ;
Bharadwaj, PK .
INORGANIC CHEMISTRY, 2004, 43 (15) :4626-4630
[6]   Tetraethynylbenzo[2,1,3]thiadiazole [J].
Bangcuyo, CG ;
Smith, MD ;
Bunz, UHF .
SYNLETT, 2004, (01) :169-172
[7]   A re-evaluation of the photophysical properties of 1,4-bis(phenylethynyl)benzene: A model for poly(phenyleneethynylene) [J].
Beeby, A ;
Findlay, K ;
Low, PJ ;
Marder, TB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (28) :8280-8284
[8]   Toward a rational design of poly(2,7-carbazole) derivatives for solar cells [J].
Blouin, Nicolas ;
Michaud, Alexandre ;
Gendron, David ;
Wakim, Salem ;
Blair, Emily ;
Neagu-Plesu, Rodica ;
Belletete, Michel ;
Durocher, Gilles ;
Tao, Ye ;
Leclerc, Mario .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) :732-742
[9]   Fluorescent conjugated polymers that incorporate substituted 2,1,3-benzooxadiazole and 2,1,3-benzothiadiazole units [J].
Bouffard, Jean ;
Swager, Timothy M. .
MACROMOLECULES, 2008, 41 (15) :5559-5562
[10]   Synthesis of Conjugated Polymers for Organic Solar Cell Applications [J].
Cheng, Yen-Ju ;
Yang, Sheng-Hsiung ;
Hsu, Chain-Shu .
CHEMICAL REVIEWS, 2009, 109 (11) :5868-5923