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Molecules 2007, 12(4), 723-734; doi:10.3390/12040723
Article

Multi-step Redox Systems with NIR-Fluorescence Based on 4H-Imidazoles

 and *
Institute of Organic and Makromolecular Chemistry, Friedrich-Schiller University D-07743 Jena, Humboldtstr. 10, Germany
* Author to whom correspondence should be addressed.
Received: 22 March 2007 / Revised: 29 March 2007 / Accepted: 29 March 2007 / Published: 5 April 2007
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Abstract

A new class of 4H-imidazoles was synthesized starting from fused-ring aromatic dinitriles. Strong bathochromic shifts of the longest wavelength absorptions were observed in the corresponding UV/vis spectra due to a conversion of the merocyanine chromophores into cyanines/(aza)oxonoles upon protonation/deprotonation of the 4H-imidazoles. Novel boratetraazapentalenes were synthesized via a cyclization reaction with boron trifluoride. These mesoionic species bearing a cyanine chromophore not only show NIR-fluorescence, they also participate as part of a quasi-reversible multi-step redox system. Large calculated semiquinone formation constants KSEM (3x1010 to 5x1011) indicate a high thermodynamic stability of the corresponding radical anions (SEM).
Keywords: 4H-Imidazoles; boratetraazapentalenes; multi-step redoxsystems; NIR-fluorescence 4H-Imidazoles; boratetraazapentalenes; multi-step redoxsystems; NIR-fluorescence
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Matschke, M.; Beckert, R. Multi-step Redox Systems with NIR-Fluorescence Based on 4H-Imidazoles. Molecules 2007, 12, 723-734.

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