One-Pot Synthesis of a Mono-O,B,N-strapped BODIPY Derivative Displaying Bright Fluorescence in the Solid State

Tin­(IV) catalysis allows isolation of a boron dipyrromethene derivative bearing a solitary strap around the boron center. The conditions favor internal cyclization without contamination by side products and provide high yields of product in good purity. A phenolate-based strap imposes chirality and...

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Bibliographic Details
Published inOrganic letters Vol. 19; no. 7; pp. 1626 - 1629
Main Authors Sirbu, Dumitru, Benniston, Andrew C, Harriman, Anthony
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.04.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DYES
MOLECULAR ROTORS
SUBSTITUENTS
CHEMISTRY
PACKING
ENERGY-TRANSFER
VISCOSITY
PHOTOPHYSICAL PROPERTIES
DIPYRROMETHENEBORON DIFLUORIDE BODIPY
EMISSION
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Summary:Tin­(IV) catalysis allows isolation of a boron dipyrromethene derivative bearing a solitary strap around the boron center. The conditions favor internal cyclization without contamination by side products and provide high yields of product in good purity. A phenolate-based strap imposes chirality and causes geometrical distortion of the dipyrrin. Relatively strong fluorescence is observed for single crystals, evaporated films, and adsorbed layers. Single-crystal absorption and emission spectra resemble those observed from solution with contributions from a dimer.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00435