Synthesis and photophysical characterization of chalcogen substituted BODIPY dyes

Eduard Fron; Eduardo Coutiño-Gonzalez; Lesley Pandey; Michel Sliwa; Mark Van Der Auweraer; Frans C. De Schryver; Joice Thomas; Zeyuan Dong; Volker Leen; Mario Smet; Wim Dehaen; Tom Vosch

doi:10.1039/b900786e

Synthesis and photophysical characterization of chalcogen substituted BODIPY dyes

Eduard Fron
, Eduardo Coutiño-Gonzalez
, Lesley Pandey
, Michel Sliwa
, Mark Van Der Auweraer
, Frans C. De Schryver
, Joice Thomas
, Zeyuan Dong
, Volker Leen
, Mario Smet
, Wim Dehaen
, Tom Vosch

KU Leuven

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

Abstract

Synthetic details and stationary and time-resolved photophysical properties of five BODIPY derivatives containing chalcogen atoms are presented. The photophysical data are compared to those of a chlorine atom containing BODIPY, acting as a reference. A strong impact in the HOMO-LUMO transition energy is achieved via nucleophilic substitution with chalcogen based units. Going from oxygen to tellurium a bathochromic shift in both absorption and emission spectra from the green to the near infrared region was observed. By employing fluorescence single photon timing experiments in two solvents of different polarity, the excited state dynamics and their solvent dependence indicate the presence of a mechanism involving a photoinduced charge transfer that dramatically affects the optical radiative processes of these derivatives.

Original language	English
Pages (from-to)	1490-1496
Number of pages	7
Journal	New Journal of Chemistry
Volume	33
Issue number	7
DOIs	https://doi.org/10.1039/b900786e
Publication status	Published - 1 Jan 2009

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title = "Synthesis and photophysical characterization of chalcogen substituted BODIPY dyes",

abstract = "Synthetic details and stationary and time-resolved photophysical properties of five BODIPY derivatives containing chalcogen atoms are presented. The photophysical data are compared to those of a chlorine atom containing BODIPY, acting as a reference. A strong impact in the HOMO-LUMO transition energy is achieved via nucleophilic substitution with chalcogen based units. Going from oxygen to tellurium a bathochromic shift in both absorption and emission spectra from the green to the near infrared region was observed. By employing fluorescence single photon timing experiments in two solvents of different polarity, the excited state dynamics and their solvent dependence indicate the presence of a mechanism involving a photoinduced charge transfer that dramatically affects the optical radiative processes of these derivatives.",

author = "Eduard Fron and Eduardo Couti{\~n}o-Gonzalez and Lesley Pandey and Michel Sliwa and \{Van Der Auweraer\}, Mark and \{De Schryver\}, \{Frans C.\} and Joice Thomas and Zeyuan Dong and Volker Leen and Mario Smet and Wim Dehaen and Tom Vosch",

year = "2009",

month = jan,

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doi = "10.1039/b900786e",

language = "English",

volume = "33",

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TY - JOUR

T1 - Synthesis and photophysical characterization of chalcogen substituted BODIPY dyes

AU - Fron, Eduard

AU - Coutiño-Gonzalez, Eduardo

AU - Pandey, Lesley

AU - Sliwa, Michel

AU - Van Der Auweraer, Mark

AU - De Schryver, Frans C.

AU - Thomas, Joice

AU - Dong, Zeyuan

AU - Leen, Volker

AU - Smet, Mario

AU - Dehaen, Wim

AU - Vosch, Tom

PY - 2009/1/1

Y1 - 2009/1/1

N2 - Synthetic details and stationary and time-resolved photophysical properties of five BODIPY derivatives containing chalcogen atoms are presented. The photophysical data are compared to those of a chlorine atom containing BODIPY, acting as a reference. A strong impact in the HOMO-LUMO transition energy is achieved via nucleophilic substitution with chalcogen based units. Going from oxygen to tellurium a bathochromic shift in both absorption and emission spectra from the green to the near infrared region was observed. By employing fluorescence single photon timing experiments in two solvents of different polarity, the excited state dynamics and their solvent dependence indicate the presence of a mechanism involving a photoinduced charge transfer that dramatically affects the optical radiative processes of these derivatives.

AB - Synthetic details and stationary and time-resolved photophysical properties of five BODIPY derivatives containing chalcogen atoms are presented. The photophysical data are compared to those of a chlorine atom containing BODIPY, acting as a reference. A strong impact in the HOMO-LUMO transition energy is achieved via nucleophilic substitution with chalcogen based units. Going from oxygen to tellurium a bathochromic shift in both absorption and emission spectra from the green to the near infrared region was observed. By employing fluorescence single photon timing experiments in two solvents of different polarity, the excited state dynamics and their solvent dependence indicate the presence of a mechanism involving a photoinduced charge transfer that dramatically affects the optical radiative processes of these derivatives.

U2 - 10.1039/b900786e

DO - 10.1039/b900786e

M3 - Article

AN - SCOPUS:67651146416

SN - 1144-0546

VL - 33

SP - 1490

EP - 1496

JO - New Journal of Chemistry

JF - New Journal of Chemistry

IS - 7

ER -

Synthesis and photophysical characterization of chalcogen substituted BODIPY dyes

Abstract

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