Synthesis of novel quinaldine-based squaraine dyes: effect of substituents and role of electronic factors

Jyothish, Kuthanapillil ; Arun, Kalliat T. ; Ramaiah, Danaboyina (2004) Synthesis of novel quinaldine-based squaraine dyes: effect of substituents and role of electronic factors Organic Letters, 6 (22). pp. 3965-3968. ISSN 1523-7060

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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol048411y

Related URL: http://dx.doi.org/10.1021/ol048411y

Abstract

Condensation of squaric acid with quinaldinium salts containing electron-donating substituents gave only the semisquaraines. However, with salts possessing electronegative and electron-withdrawing groups, the squaraine dyes were isolated in quantitative yields. The semisquaraines formed undergo condensation with highly nucleophilic salts yielding the unsymmetrical squaraine dyes. These results demonstrate the role of electronic factors and provide valuable information for the design of efficient squaraine-based sensitizers that can have potential applications in photodynamic therapy.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:63609
Deposited On:29 Sep 2011 04:00
Last Modified:29 Sep 2011 04:00

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