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PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
11
pubmed:dateCreated
2005-5-26
pubmed:abstractText
An extensive series of silyl-protected cyanoethynylethenes (CEEs) and N,N-dimethylanilino donor-substituted CEEs have been synthesized. More extended chromophores were constructed by selective silyl deprotection and subsequent oxidative acetylenic coupling. The strong electron-accepting nature of the CEEs was revealed by a combination of 13C NMR spectroscopic and electrochemistry measurements. Donor-substituted CEEs display strong intramolecular charge-transfer (CT) character, resulting in intense, bathochromically shifted CT bands in the UV/Vis spectrum. Their structural diversity establishes them as suitable models for the study of pi-conjugation and band gap tuning in strong charge-transfer chromophores. The extent of pi-conjugation in the donor-substituted CEEs was investigated by a combination of ground-state techniques, such as X-ray crystallography, electrochemistry, B3 LYP calculations, and NMR spectroscopy. The comparison of these ground-state results with the features observed in the UV/Vis spectra reveals that-contrary to expectations-more extensive pi-conjugation can lead to larger band gaps in molecules with strong donor and acceptor moieties.
pubmed:language
eng
pubmed:journal
pubmed:status
PubMed-not-MEDLINE
pubmed:month
May
pubmed:issn
0947-6539
pubmed:author
pubmed:issnType
Print
pubmed:day
20
pubmed:volume
11
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
3325-41
pubmed:dateRevised
2009-8-4
pubmed:year
2005
pubmed:articleTitle
Donor-substituted cyanoethynylethenes: pi-conjugation and band-gap tuning in strong charge-transfer chromophores.
pubmed:affiliation
Laboratorium für Organische Chemie, ETH-Hönggerberg, HCI, 8093 Zürich, Switzerland.
pubmed:publicationType
Journal Article