D-π-A-A-π-D prototype 2,2'-bipyridine dyads exhibiting large structure and environment sensitive fluorescence: synthesis, photophysics and computation

Sarma, Monima ; Chatterjee, Tanmay ; Ghanta, Susanta ; Das, S. K. (2011) D-π-A-A-π-D prototype 2,2'-bipyridine dyads exhibiting large structure and environment sensitive fluorescence: synthesis, photophysics and computation Journal of Organic Chemistry, 77 (1). pp. 432-444. ISSN 0022-3263

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Official URL: http://pubs.acs.org/toc/joceah/current#d473e26

Abstract

A series of 4,4'-π -conjugated-2,2'-bipyridine chromophores (MS 1-8) were synthesized, and their photophysical and thermal properties were investigated. The title "push-pull' chromophores", except MS 1, were integrated with both alkoxy and alkylamino donor functionalities that differ in their donation capabilities. The oligophenylenevinylene (OPV) chromophores MS 4-8 are associated with a p-extended backbone in which the position and the number of alkoxy donors were systematically varied. All of the studied systems possess a D-π -A-A-π -D dyad archetype in which the A-A is the central 2,2'-bipyridine acceptor core that is electronically attached with the donor termini through p-linkers. The fluorescence quantum yields of the synthesized chromophores are found to be sensitive to the molecular archetype and the solvent medium. Out of the eight fluorescent compounds reported in this article, the compound MS 5 exhibits fluorescence in the solid state also. The modulating effect of the nature, position, and number of donor functionalities on the optical properties of these classes of compounds has further been comprehended on the basis of DFT and TD-DFT computation in a solvent reaction field.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:80015
Deposited On:31 Jan 2012 06:25
Last Modified:31 Jan 2012 06:25

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