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Synthesis of thiophene-substituted aza-BODIPYs and their optical and electrochemical properties

Abstract:
A series of novel thiophene-substituted aza-BODIPY dyes were synthesized by means of a standard procedure and complemented by a Stille-coupling of a brominated species with 2-tributylstannylthiophene. The optical as well as the electrochemical properties of the compounds were investigated and compared to result of density functional theory (DFT) calculations. The influence of the thiophene substituents is discussed in dependence of the position at the aza-BODIPY core regarding the HOMO and LUMO frontier orbitals. The different distributions of the HOMO and LUMO coefficients over the BODIPY core lead to a variable influence of the thiophene substituents on the HOMO and LUMO energies, being the origin of the tunable optical and electrochemical properties. © 2011 Elsevier Ltd. All rights reserved.
Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1016/j.tet.2011.06.100

Authors


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Institution:
University of Oxford
Division:
MPLS
Department:
Physics
Sub department:
Condensed Matter Physics
Role:
Author


Publisher:
Elsevier
Journal:
Tetrahedron More from this journal
Volume:
67
Issue:
37
Pages:
7148-7155
Publication date:
2011-09-16
DOI:
EISSN:
1464-5416
ISSN:
0040-4020


Language:
English
Keywords:
Pubs id:
pubs:405367
UUID:
uuid:51b52f1f-961b-4216-bfb0-eb35bd163896
Local pid:
pubs:405367
Source identifiers:
405367
Deposit date:
2013-09-26

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