Structure-property relationships of acylated asymmetric dithienophospholes

被引：9

作者：

Gordon, Terry J. ^{[1
]}

Szabo, Lisa D. ^{[1
]}

Linder, Thomas ^{[1
]}

Berlinguette, Curtis P. ^{[1
]}

Baumgartner, Thomas ^{[1
]}

机构：

[1] Univ Calgary, Dept Chem, Inst Sustainable Energy Environm & Econ, Calgary, AB T2N 1N4, Canada

来源：

COMPTES RENDUS CHIMIE | 2010年 / 13卷 / 8-9期

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

Phosphorus heterocycles; Materials science; Acylation; Fluorescence; Density functional calculations; Cross-coupling; BAND-GAP; BUILDING-BLOCK; LUMINESCENT; OLIGOMERS; EMISSION; SYSTEMS;

D O I：

10.1016/j.crci.2010.04.023

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Friedel-Crafts acylation was found to be an effective way to selectively access monofunctionalized dithienophospholes. Absorption and emission properties of the acylated compounds exhibited high extinction coefficients, relative to unsubstituted dithienophosphole and bathochromic shifts when in the presence of Lewis-acids, e.g., AlCl3 and BF3, effectively demonstrating that the emissive characteristics could be tuned. Subsequent treatment of the asymmetric mono-substituted compounds with N-bromosuccinimide, yielded materials that were later employed in Ni-catalyzed Yamamoto cross-coupling reactions. The resulting cross-coupled material exhibited a substantial increase in its extinction coefficient as well as a further red-shifted absorbance and emission profile, relative to the mono-functionalized phosphole. (C) 2010 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.

引用

页码：971 / 979

页数：9