Rational design of visible and NIR distyryl-BODIPY dyes from a novel fluorinated platform

A new series of distyryl-BODIPY has been rationally designed and synthesised from a novel fluorinated platform, 8-pentafluorophenyl BODIPY, which has enhanced reactivity in the presence of both electron rich, and for the first time, electron deficient aldehydes. The pentafluorobenzene leads to large...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 8; no. 20; pp. 4546 - 4553
Main Authors Galangau, Olivier, Dumas-Verdes, Cecile, Meallet-Renault, Rachel, Clavier, Gilles
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.10.2010
Royal Society of Chemistry
Subjects
Chemical Sciences
Chemistry
Chemistry, Organic
Organic chemistry
Physical Sciences
Science & Technology
ELECTROCHEMISTRY
EFFICIENT ENERGY-TRANSFER
POLARIZABILITY SP
MOLECULE
STYRYL
SENSOR
DERIVATIVES
HIGHLY EFFICIENT
STATE FLUORESCENCE
RATIOMETRIC FLUORESCENT CHEMOSENSOR
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Summary:A new series of distyryl-BODIPY has been rationally designed and synthesised from a novel fluorinated platform, 8-pentafluorophenyl BODIPY, which has enhanced reactivity in the presence of both electron rich, and for the first time, electron deficient aldehydes. The pentafluorobenzene leads to larger red shifts of absorption and emission compared to previously reported analogues. The reactivity and spectroscopic results have been rationalised with quantum mechanics calculation. The fluorescence sensitivity of one derivative to acidity is also presented.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/c004812g