Next Article in Journal
Synthesis of (R)-Dihydropyridones as Key Intermediates for an Efficient Access to Piperidine Alkaloids
Previous Article in Journal
Synthesis and X-ray Structure of the Inclusion Complex of Dodecamethylcucurbit[6]uril with 1,4-Dihydroxybenzene
Article Menu

Export Article

Open AccessArticle
Molecules 2007, 12(4), 723-734;

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

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
Full-Text   |   PDF [129 KB, uploaded 18 June 2014]   |  


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). View Full-Text
Keywords: 4H-Imidazoles; boratetraazapentalenes; multi-step redoxsystems; NIR-fluorescence 4H-Imidazoles; boratetraazapentalenes; multi-step redoxsystems; NIR-fluorescence

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Share & Cite This Article

MDPI and ACS Style

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

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top