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Efficient synthesis of solid-emissive Boron–Fluorine derivatives

Authors :
Qiong Cao
Zhangshuang Deng
Sa Wang
Kun Zou
Xiaohong Chen
Shuzhang Xiao
Nianyu Huang
Source :
Tetrahedron Letters. 54:4116-4120
Publication Year :
2013
Publisher :
Elsevier BV, 2013.

Abstract

A highly solid-emissive Boron–Fluorine scaffold with two conjugated alkyne groups ( BOPIM-S ) is facilely synthesized, which shows enhanced fluorescent intensity compared to the BOPIM dye without alkyne units. According to X-ray single crystal analysis, the terminal alkyne groups interact with atoms B, F, C and N on neighbouring molecules, producing a rigid rectangular structure, which helps to avoid energy loss via non-irradiative decay. Furthermore, BOPIM-S can undergo copper catalysed alkyne–azide-cycloaddition (CuAAC) chemistry with aromatic azides to produce conjugated molecules with high yields. According to absorption and fluorescent measurements, all these compounds synthesized by CuAAC emit large Stokes shift (over 100 nm) both in solution and in solid state. But the electronic environments of terminal aromatic rings slightly affect their photophysical properties.

Details

ISSN :
00404039
Volume :
54
Database :
OpenAIRE
Journal :
Tetrahedron Letters
Accession number :
edsair.doi...........7384126d0eccf7d584d0ce52b244c590