Synthesis of a Luminescent Arsolo[2,3-d:5,4-d']bis(thiazole) Building Block and Comparison to Its Phosphole Analogue
File(s)
Accepted version
Author(s)
Green, JP
Cryer, SJ
Marafie, J
White, AJP
Heeney, M
Type
Journal Article
Abstract
The synthesis of 4-phenyl-4H-arsolo[2,3-d:5,4-d′]bis(thiazole) is reported, and its properties are compared to those of the previously prepared phosphole analogue. By comparison of their single-crystal structures, the harmonic oscillator model of heterocyclic electron delocalization (HOMHED) was used to directly compare the aromatic character of the two systems. The findings demonstrate that, although both compounds can be considered aromatic, the phosphole-containing compound had a greater degree of aromatic character than its arsole analogue. The arsole derivative exhibited excellent stability in ambient air with no formation of the arsole oxide observed upon storage. The absorption and photoluminescence spectra of the arsole derivate were subtly altered in comparison to the phosphole derivative, suggesting that changing pnictogenic atoms in such fused-ring systems to heavier analogues could be a viable way of tuning both the ambient stability and optoelectronic properties of such materials.
Date Issued
2017-07-24
Date Acceptance
2017-06-05
Citation
Organometallics, 2017, 36 (14), pp.2632-2636
ISSN
0276-7333
Publisher
American Chemical Society
Start Page
2632
End Page
2636
Journal / Book Title
Organometallics
Volume
36
Issue
14
Copyright Statement
Copyright © 2017 American Chemical Society
Subjects
Science & Technology
Physical Sciences
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry
PI-CONJUGATED MATERIALS
ORGANIC ELECTRONICS
HOMA INDEX
HETEROCYCLES
AROMATICITY
POLYMER
Publication Status
Published