Please use this identifier to cite or link to this item: https://dspace.iiti.ac.in/handle/123456789/9344
Title: Tuning of the HOMO-LUMO gap of donor-substituted symmetrical and unsymmetrical benzothiadiazoles
Authors: Misra, Rajneesh
Keywords: Electrolytic reduction;Infrared devices;Benzothiadiazoles;Charge transfer bands;Computational properties;Computational studies;Donor-acceptor interaction;Electrochemical reductions;Near infrared region;Single-photon absorptions;Steel beams and girders
Issue Date: 2014
Publisher: Royal Society of Chemistry
Citation: Misra, R., & Gautam, P. (2014). Tuning of the HOMO-LUMO gap of donor-substituted symmetrical and unsymmetrical benzothiadiazoles. Organic and Biomolecular Chemistry, 12(29), 5448-5457. doi:10.1039/c4ob00629a
Abstract: This article reports the design and synthesis of donor-substituted symmetrical and unsymmetrical benzothiadiazoles (BTDs) 5-12 of type D-π-A-D, D1-π-A-D2, D1-A1-A 2-D2, D-A1-A2-D and D-A 1-A2-A1-D by Ullmann, Suzuki and cycloaddition-retroelectrocyclization reactions. The photophysical, electrochemical and computational properties were studied and show substantial donor-acceptor interaction. Their single photon absorption show strong charge transfer bands in the near-infrared (NIR) region and the electrochemical reduction show multiple reduction waves. The optical HOMO-LUMO gap of BTDs 5-12 was found to be a function of the number and nature of the acceptors. Computational studies reveal that strong cyano-based acceptors, dicyanoquinodimethane (DCNQ) and tetracyanobutadiene (TCBD) lower the LUMO level in BTDs 7-12, which results in a low HOMO-LUMO gap compared to acetylene linked BTDs 5 and 6. The BTDs with carbazole and single TCBD and DCNQ acceptors show better thermal stability. This journal is © the Partner Organisations 2014.
URI: https://doi.org/10.1039/c4ob00629a
https://dspace.iiti.ac.in/handle/123456789/9344
ISSN: 1477-0520
Type of Material: Journal Article
Appears in Collections:Department of Chemistry

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