title: 6-Hydroxyindole-based borondipyrromethene: synthesis and spectroscopic studies.
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.
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science & Technology, Shanghai, 200237, PR China. zhaocchang@ecust.edu.cn
authors.forename: Chunchang
authors.initials: C
authors.lastname: Zhao
authors.forename: Peng
authors.initials: P
authors.lastname: Feng
authors.forename: Jian
authors.initials: J
authors.lastname: Cao
authors.forename: Yulin
authors.initials: Y
authors.lastname: Zhang
authors.forename: Xuzhe
authors.initials: X
authors.lastname: Wang
authors.forename: Yang
authors.initials: Y
authors.lastname: Yang
authors.forename: Yanfen
authors.initials: Y
authors.lastname: Zhang
authors.forename: Jinxin
authors.initials: J
authors.lastname: Zhang
mesh_terms: D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; D007211:Indoles; C571206:6-hydroxyindole