Photophysics of 3,5-diphenoxy substituted BODIPY dyes in solution

Taoufik Rohand; Jess Lycoops; Steve Smout; Els Braeken; Michel Sliwa; Mark Van Der Auweraer; Wim Dehaen; Wim M. De Borggraeve; Noël Boens

doi:10.1039/b705921c

Photophysics of 3,5-diphenoxy substituted BODIPY dyes in solution

Taoufik Rohand
, Jess Lycoops
, Steve Smout
, Els Braeken
, Michel Sliwa
, Mark Van Der Auweraer
, Wim Dehaen
, Wim M. De Borggraeve
, Noël Boens

KU Leuven

Research output: Contribution to journal › Article › peer-review

Abstract

We have prepared two fluorescent dyes derived from 8-(4-tolyl)-4,4- difluoro-4-bora-3a,4a-diaza-s-indacene with phenoxy and (o-bromo)phenoxy substituents at the 3,5-positions by a novel nucleophilic substitution reaction of the corresponding 3,5-dichloroBODIPY analogue. UV-vis absorption, steady-state and time-resolved fluorimetry have been used to investigate their solvent-dependent photophysical properties. The two BODIPY derivatives show narrow absorption and emission bands and display small Stokes shifts. The substituents at the 3,5-positions (phenoxy in 1 and o-bromophenoxy in 2) have a minor effect on the fluorescence quantum yields (0.16-0.40 for 1, 0.17-0.44 for 2) and lifetimes (1.09-2.51 ns for 1, 1.11-2.78 ns for 2). For both compounds, the fluorescence rate constant equals (1.5 ± 0.1) × 10⁸ s^-1.

Original language	English
Pages (from-to)	1061-1066
Number of pages	6
Journal	Photochemical and Photobiological Sciences
Volume	6
Issue number	10
DOIs	https://doi.org/10.1039/b705921c
Publication status	Published - 1 Jan 2007
Externally published	Yes

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@article{739b4f3b829f4147af43676d280ff314,

title = "Photophysics of 3,5-diphenoxy substituted BODIPY dyes in solution",

abstract = "We have prepared two fluorescent dyes derived from 8-(4-tolyl)-4,4- difluoro-4-bora-3a,4a-diaza-s-indacene with phenoxy and (o-bromo)phenoxy substituents at the 3,5-positions by a novel nucleophilic substitution reaction of the corresponding 3,5-dichloroBODIPY analogue. UV-vis absorption, steady-state and time-resolved fluorimetry have been used to investigate their solvent-dependent photophysical properties. The two BODIPY derivatives show narrow absorption and emission bands and display small Stokes shifts. The substituents at the 3,5-positions (phenoxy in 1 and o-bromophenoxy in 2) have a minor effect on the fluorescence quantum yields (0.16-0.40 for 1, 0.17-0.44 for 2) and lifetimes (1.09-2.51 ns for 1, 1.11-2.78 ns for 2). For both compounds, the fluorescence rate constant equals (1.5 ± 0.1) × 108 s-1.",

author = "Taoufik Rohand and Jess Lycoops and Steve Smout and Els Braeken and Michel Sliwa and \{Van Der Auweraer\}, Mark and Wim Dehaen and \{De Borggraeve\}, \{Wim M.\} and No{\"e}l Boens",

year = "2007",

month = jan,

day = "1",

doi = "10.1039/b705921c",

language = "English",

volume = "6",

pages = "1061--1066",

journal = "Photochemical and Photobiological Sciences",

issn = "1474-905X",

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}

TY - JOUR

T1 - Photophysics of 3,5-diphenoxy substituted BODIPY dyes in solution

AU - Rohand, Taoufik

AU - Lycoops, Jess

AU - Smout, Steve

AU - Braeken, Els

AU - Sliwa, Michel

AU - Van Der Auweraer, Mark

AU - Dehaen, Wim

AU - De Borggraeve, Wim M.

AU - Boens, Noël

PY - 2007/1/1

Y1 - 2007/1/1

N2 - We have prepared two fluorescent dyes derived from 8-(4-tolyl)-4,4- difluoro-4-bora-3a,4a-diaza-s-indacene with phenoxy and (o-bromo)phenoxy substituents at the 3,5-positions by a novel nucleophilic substitution reaction of the corresponding 3,5-dichloroBODIPY analogue. UV-vis absorption, steady-state and time-resolved fluorimetry have been used to investigate their solvent-dependent photophysical properties. The two BODIPY derivatives show narrow absorption and emission bands and display small Stokes shifts. The substituents at the 3,5-positions (phenoxy in 1 and o-bromophenoxy in 2) have a minor effect on the fluorescence quantum yields (0.16-0.40 for 1, 0.17-0.44 for 2) and lifetimes (1.09-2.51 ns for 1, 1.11-2.78 ns for 2). For both compounds, the fluorescence rate constant equals (1.5 ± 0.1) × 108 s-1.

AB - We have prepared two fluorescent dyes derived from 8-(4-tolyl)-4,4- difluoro-4-bora-3a,4a-diaza-s-indacene with phenoxy and (o-bromo)phenoxy substituents at the 3,5-positions by a novel nucleophilic substitution reaction of the corresponding 3,5-dichloroBODIPY analogue. UV-vis absorption, steady-state and time-resolved fluorimetry have been used to investigate their solvent-dependent photophysical properties. The two BODIPY derivatives show narrow absorption and emission bands and display small Stokes shifts. The substituents at the 3,5-positions (phenoxy in 1 and o-bromophenoxy in 2) have a minor effect on the fluorescence quantum yields (0.16-0.40 for 1, 0.17-0.44 for 2) and lifetimes (1.09-2.51 ns for 1, 1.11-2.78 ns for 2). For both compounds, the fluorescence rate constant equals (1.5 ± 0.1) × 108 s-1.

U2 - 10.1039/b705921c

DO - 10.1039/b705921c

M3 - Article

AN - SCOPUS:34948853763

SN - 1474-905X

VL - 6

SP - 1061

EP - 1066

JO - Photochemical and Photobiological Sciences

JF - Photochemical and Photobiological Sciences

IS - 10

ER -

Photophysics of 3,5-diphenoxy substituted BODIPY dyes in solution

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