Influence of Conjugation Axis on the Optical and Electronic Properties of Aryl-Substituted Benzobisoxazoles

被引：37

作者：

Tlach, Brian C. ^{[1
]}

Tomlinson, Aimee L. ^{[2
]}

Ryno, Alden G. ^{[2
]}

Knoble, Dawn D. ^{[1
]}

Drochner, Dana L. ^{[1
]}

Krager, Kyle J.

Jeffries-EL, Malika ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50010 USA

[2] Univ North Georgia, Dept Chem, Dahlonega, GA 30597 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 13期

基金：

美国国家科学基金会;

关键词：

THIN-FILM TRANSISTORS; PHOTOPHYSICAL PROPERTIES; EFFICIENT SYNTHESIS; SOLAR-CELLS; FLUOROPHORES; FLUORESCENCE; CRUCIFORMS; DESIGN; TETRAKIS(PHENYLETHYNYL)BENZENES; SPECTROSCOPY;

D O I：

10.1021/jo4007927

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Six different 2,6-diethyl-4,8-diarylbenzo[1,2-d:4,5-d']bis(oxazoles) and four different 2,4,6,8-tetraarylbenzobisoxazoles were synthesized in two steps: a Lewis acid catalyzed orthoester cyclization followed by a Suzuki or Stille cross-coupling with various arenes. The influence of aryl group substitution and/or conjugation axis variation on the optical and electronic properties of these benzobis(oxazole) (BBO) compounds was evaluated Structural modifications could be used to alter the HOMO, LUMO, and band gap over a range of 1.0, 0.5, and 0.5 eV, respectively. However, depending on the location and identity of the substituent, the HOMO level Can be altered without significantly impacting the LUMO level. This is supported by the calculated frontier molecular orbitals. Our results indicate that the FMOs and band gaps of benzobisoxazoles can be readily modified either jointly or individually.

引用

收藏

页码：6570 / 6581

页数：12

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