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Tuning the HOMO–LUMO gap of donor-substituted benzothiazoles.
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Dec2014, Vol. 55 Issue 50, p6827-6830. 4p. - Publication Year :
- 2014
-
Abstract
- A series of push–pull benzothiazoles were designed and synthesized by the Pd-catalyzed Sonogashira cross-coupling and [2+2] cycloaddition–retroelectrocyclization reactions. The photonic and electrochemical properties of these systems exhibit strong donor–acceptor interaction. The BTs 5 – 8 show strong intramolecular charge-transfer in the near-infrared (NIR) region. The absorption studies indicate systematic lowering of the optical HOMO–LUMO gap with increase in acceptor strength. The computational studies reveal that incorporation of strong acceptors TCNE and TCNQ results in substantial stabilization of the LUMO level compared to the HOMO level, leading to the low HOMO–LUMO gap and bathochromic shift of the absorption spectrum. The TCBD and DCNQ linked BTs 5 – 8 exhibit multi-step redox waves and improved thermal stability. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 55
- Issue :
- 50
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 99507075
- Full Text :
- https://doi.org/10.1016/j.tetlet.2014.10.094