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Meso-thienyl and furyl rotor effects in BF2-chelated dipyrrin dyes: solution spectroscopic studies and X-ray structural packing analysis of isomer and congener effects

Lookup NU author(s): Professor Andrew Benniston


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Well-defined discrete fluorescent molecular systems with very subtle steric/electronic differences are interesting when considering solid-state packing and solution substituent effects. Herein, we report the synthesis and characterization of four 4,4-difluoro-1,3,5,7-tetramethyl-8-(C4H3 X)-4-bora-3a,4a-diaza-s-indacene complexes (X?=?O, S). Various NMR spectroscopic experiments were used to assign all relevant atoms (CD2Cl2): 19F, 11B, 1H, 13C, 13CH undecoupled, 1H1H COSY, 1H1H NOESY, 1H13C HSQC, and 1H13C HMBC NMR spectroscopy. UV-Vis and fluorescence studies were undertaken for all compounds. Chemical shift differences were found between isomers and congeners; for congeners, aromatic d differences were attributed to electron-poor character. Also, compounds 14 were studied crystallographically. In the solid state, internal dihedral planes and intermolecular packing patterns can be compared.

Publication metadata

Author(s): Jun T, Kim K, Lee KM, Benniston AC, Churchill DG

Publication type: Article

Publication status: Published

Journal: Journal of Coordination Chemistry

Year: 2012

Volume: 65

Issue: 24

Pages: 4299-4314

Print publication date: 01/11/2012

ISSN (print): 0095-8972

ISSN (electronic): 1029-0389

Publisher: Taylor & Francis Ltd.


DOI: 10.1080/00958972.2012.740023


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Funder referenceFunder name
Dong-a Pencil Co., Daejeon, Korea
University of Newcastle
2009-0070330National Research Foundation
2010-0013660National Research Foundation
2011-0017280National Research Foundation