Synthesis, structural characterization, and spectroscopic properties of the ortho, meta, and para isomers of 8‐(HOCH2‐C6H4)‐BODIPY and 8‐(MeOC6H4)‐BODIPY

作者: Robinson I. Roacho , Alejandro J. Metta-Magaña , Eduardo Peña-Cabrera , Keith H. Pannell

DOI: 10.1002/POC.3095

关键词:

摘要: Fluorescent members of the 4, 4-difluoro-4-bora-3a, 4a-diaza-s-indacene (BODIPY) family are widely used for a range markers, dyes, and sensors. The capacity to substitute basic framework is an attractive feature permitting differently substituted materials be formed. New isomeric BODIPYs, o-, m-, p-8-[R-C6H4]-BODIPY (R = CH2OH, 2a (o), 2b (m), 2c (p); R = OMe, 3a 3b 3c (p)), have been synthesized characterized by nuclear magnetic resonance, absorbance emission spectroscopy, single crystal X-ray diffraction. o-isomers very high quantum yield in non-polar solvents, while m- p- analogs showed weak fluorescence under same conditions. Spectroscopic analysis, as well structural characterization, suggested that substitution ortho-position phenyl ring sufficient increase steric hindrance hence impede rotation moiety about 8C-C axis, thereby favoring radiative compared non-radiative relaxation. Copyright © 2013 John Wiley & Sons, Ltd.

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