Journal
TETRAHEDRON
Volume 68, Issue 47, Pages 9795-9801Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.09.011
Keywords
Fluorescent; BODIPY; Dye; X-ray; Thiophene-fused
Categories
Funding
- National Natural Science Foundation of China [20872026]
- Hi-Tech Research and Development Program of China (863 Plan) [2009AA02Z308]
- Shanghai Pujiang Talent Plan Project [09PJD008]
- Sino Swiss Science and Technology Cooperation (SSSTC) [EG 30-032010]
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A series of non-symmetric BODIPYs containing thieno[3,2-b]pyrrole moiety were synthesized in 21-63% yields. The absorption and emission maxima covered from the visible green to red region (lambda(abs)=532-647 nm: lambda(em)=547-664 nm; Phi(f)=0.19-0.45). X-ray analysis indicated that the S-C bond lengths were shorter than those of thienopyrrole and thienohelicene by 0.03-0.05 angstrom. The crystal packing pattern suggested that strong pi-pi interaction, intermolecular C-H center dot center dot center dot F interaction, and weak S center dot center dot center dot pi interaction existed. The tunable emission was achieved by structure modifications. Oxidation of BODIPY (lambda(em)=547 nm) with m-CPBA generated thiophene-1,1-dioxide derived BODIPY (lambda(em)=528 nm). Knoevenagel-type condensation of BODIPY with N,N-dimethylaminobenzaldehyde led to BODIPY (lambda(em)=693 nm) with extended conjugation. (C) 2012 Elsevier Ltd. All rights reserved.
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