Crystal structures and solid-state fluorescence of BODIPY dyes based on Λ-shaped Tr?ger's base?

CrystEngComm Pub Date: 2012-01-12 DOI: 10.1039/C2CE06260G

Abstract

Two Λ-shaped BODIPY dyes based on Tr?ger's base, 2,8-(6H,12H-5,11-methanodibenzo[b,f]diazocineylene)-di(4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene) (DFTMB) and 2,8-(6H,12H-5,11-methanodibenzo[b,f]diazocineylene)-di(4,4-difluoro-2,6-diethyl-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene) (DFDEB), were designed and synthesized. Both compounds exhibit intense fluorescence in dilute solution and polycrystalline powder form. From the crystal structure, the impact of the substitutions at the BODIPY core on the crystal packing mode, intermolecular π–π interactions and optical behavior is compared and discussed. The results indicate that the close π–π stacking in the crystalline state has been effectively inhibited by the twisted Λ-shaped Tr?ger's base.

Graphical abstract: Crystal structures and solid-state fluorescence of BODIPY dyes based on Λ-shaped Tr?ger's base
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