Document Detail

Preparation and Acid-Responsive Photophysical Properties of T-Shaped π-Conjugated Molecules Containing a Benzimidazole Junction.
MedLine Citation:
PMID:  21815271     Owner:  NLM     Status:  Publisher    
T-shaped π-conjugated molecules with an N-methyl-benzimidazole junction have been synthesized and their acid-responsive photophysical properties owing to the change in the π-conjugation system are discussed. T-shaped π-conjugated molecules consist of two orthogonal π-conjugated systems including a phenyl thiophene extended from the 2-position and alkyl phenylenes connected through various π-spacers from the 4,7-positions of the N-methyl-benzimidazole junction. The π-spacers, such as thiophene, ethyne, and ethane, have an effect on the acid response of photophysical properties in terms of changes in conformation, excited-state energy and charge-transfer (CT) characteristics. In particular, the π-conjugated molecule with ethynyl spacers exhibited a marked redshift in the fluorescence spectrum with a large Stokes shift upon the addition of acid, whereas the other molecules showed substantial quenching. The redshift in emission was studied in detail by temperature-dependent fluorescence measurements, which indicated the transition to a CT state over the finite activation energy at the excited state. The change in the frontier molecular orbitals upon acid addition was further discussed by means of DFT calculations.
Toshifumi Inouchi; Takuya Nakashima; Masaya Toba; Tsuyoshi Kawai
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-8-3
Journal Detail:
Title:  Chemistry, an Asian journal     Volume:  -     ISSN:  1861-471X     ISO Abbreviation:  -     Publication Date:  2011 Aug 
Date Detail:
Created Date:  2011-8-4     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101294643     Medline TA:  Chem Asian J     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Graduate School of Materials Science, Nara Institute of Science and Technology, NAIST, 8916-5 Takayama, Ikoma, Nara 630-0192 (Japan), Fax: (+81) 743-72-6179.
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