6-Hydroxyindole-based borondipyrromethene: Synthesis and spectroscopic studies?

Organic & Biomolecular Chemistry Pub Date: 2011-09-30 DOI: 10.1039/C1OB06200J

Abstract

A 6-hydroxyindole-based BODIPY, named BODIPY–OH, with distinct spectroscopic characteristics is reported. Through a systematic study of the spectroscopic characteristics of BODIPY–OH and BODIPY–O? in various solvents containing an organic base, we found that the light-color of the fluorophore can be tuned over a wide range by changing the polarity of solvent/base combinations. The absorption color of the solution can be tuned over a range of 100 nm and the emission color within a wide range from 571 to 681 nm by simply converting the phenol form of BODIPY–OH to the phenolate form. Fluorescence of BODIPY–O? with high quantum yield shows relatively large Stokes shift in solvent/base combinations, which are ascribed to the excited state deprotonation from (BODIPY–OH)* to (BODIPY–O?)*, followed by emission from the ion form.

Graphical abstract: 6-Hydroxyindole-based borondipyrromethene: Synthesis and spectroscopic studies
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