rdf:type |
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lifeskim:mentions |
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pubmed:issue |
4
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pubmed:dateCreated |
2007-9-13
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pubmed:abstractText |
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 K(SEM) (3x10(10) to 5x10(11)) indicate a high thermodynamic stability of the corresponding radical anions (SEM).
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
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pubmed:status |
MEDLINE
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pubmed:issn |
1420-3049
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pubmed:author |
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pubmed:issnType |
Electronic
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pubmed:volume |
12
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
723-34
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pubmed:dateRevised |
2009-10-27
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pubmed:meshHeading |
pubmed-meshheading:17851425-Anions,
pubmed-meshheading:17851425-Boranes,
pubmed-meshheading:17851425-Electrochemistry,
pubmed-meshheading:17851425-Imidazoles,
pubmed-meshheading:17851425-Ions,
pubmed-meshheading:17851425-Kinetics,
pubmed-meshheading:17851425-Magnetic Resonance Spectroscopy,
pubmed-meshheading:17851425-Models, Chemical,
pubmed-meshheading:17851425-Oxidation-Reduction,
pubmed-meshheading:17851425-Spectrometry, Fluorescence,
pubmed-meshheading:17851425-Spectrophotometry, Ultraviolet,
pubmed-meshheading:17851425-Spectroscopy, Near-Infrared,
pubmed-meshheading:17851425-Thermodynamics,
pubmed-meshheading:17851425-Ultraviolet Rays
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pubmed:year |
2007
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pubmed:articleTitle |
Multi-step redox systems with NIR-fluorescence based on 4H-imidazoles.
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pubmed:affiliation |
Institute of Organic and Makromolecular Chemistry, Friedrich-Schiller University D-07743 Jena, Humboldtstr. 10, Germany.
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pubmed:publicationType |
Journal Article
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