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Journal Article
Research Support, Non-U.S. Gov't
Unsymmetrical and Symmetrical Push-Pull Phenothiazines.
Journal of Organic Chemistry 2017 July 8
A series of unsymmetrical and symmetrical push-pull phenothiazines (3-7) were designed and synthesized by the Pd-catalyzed Sonogashira cross-coupling reaction and subsequent [2 + 2] cycloaddition-retroelectrocyclization reaction with tetracyanoethylene (TCNE) and 7,7,8,8-tetracyanoquinodimethane (TCNQ). The effect of systematic variation of the number and nature of cyano-based acceptor TCNE and TCNQ units on the photophysical, electrochemical, and computational studies was investigated. The single-photon absorption on phenothiazines 3-7 reveals that substitution of 1,1,4,4-tetracyanobutadiene (TCBD) and a cyclohexa-2,5-diene-1,4-diylidene-expanded TCBD unit results in strong intramolecular charge transfer and lowering of the LUMO energy level. The TCBD-linked and cyclohexa-2,5-diene-1,4-diylidene-expanded TCBD-linked phenothiazines 3-7 exhibit multiredox waves. The computational studies on phenothiazines 3-7 exhibit substantial stabilization of the LUMO with the increase in acceptor strength, which results in lowering of the HOMO-LUMO gap.
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