MegaStokes BODIPY-triazoles as environmentally sensitive turn-on fluorescent dyes

Jun Cheng Er; Mui Kee Tang; Chee Geng Chia; Huimin Liew; Marc Vendrell; Young-Tae Chang

doi:10.1039/c3sc22166k

MegaStokes BODIPY-triazoles as environmentally sensitive turn-on fluorescent dyes

Jun Cheng Er, Mui Kee Tang, Chee Geng Chia, Huimin Liew, Marc Vendrell^*, Young-Tae Chang

^*Corresponding author for this work

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

Abstract

A novel class of triazole-derivatized BODIPY compounds have been synthesized on solid-phase by employing mild reaction conditions based on the copper-catalyzed azide-alkyne cycloaddition. The resulting BODIPY-triazoles exhibited MegaStokes shifts (up to 160 nm) and remarkable environmentally sensitive quantum yield increments that asserted their potential as turn-on fluorescent sensors. Out of a library of 120 compounds, we identified BDC-9 as a fluorescent chemosensor with high sensitivity and remarkable species-selectivity towards human serum albumin. These results validate MegaStokes BODIPY dyes as new fluorophores for the development of environmentally sensitive fluorescent probes.

Original language	English
Pages (from-to)	2168-2176
Number of pages	9
Journal	Chemical Science
Volume	4
Issue number	5
DOIs	https://doi.org/10.1039/c3sc22166k
Publication status	Published - 2013

Keywords / Materials (for Non-textual outputs)

HUMAN-SERUM-ALBUMIN
CRYSTALLOGRAPHIC ANALYSIS REVEALS
QUANTUM-CHEMICAL CALCULATIONS
SPECIES-DEPENDENT BINDING
DRUG-BINDING
CRYSTAL-STRUCTURE
STRUCTURAL BASIS
ENERGY-TRANSFER
FATTY-ACIDS
SPECTRAL PROPERTIES

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title = "MegaStokes BODIPY-triazoles as environmentally sensitive turn-on fluorescent dyes",

abstract = "A novel class of triazole-derivatized BODIPY compounds have been synthesized on solid-phase by employing mild reaction conditions based on the copper-catalyzed azide-alkyne cycloaddition. The resulting BODIPY-triazoles exhibited MegaStokes shifts (up to 160 nm) and remarkable environmentally sensitive quantum yield increments that asserted their potential as turn-on fluorescent sensors. Out of a library of 120 compounds, we identified BDC-9 as a fluorescent chemosensor with high sensitivity and remarkable species-selectivity towards human serum albumin. These results validate MegaStokes BODIPY dyes as new fluorophores for the development of environmentally sensitive fluorescent probes.",

keywords = "HUMAN-SERUM-ALBUMIN, CRYSTALLOGRAPHIC ANALYSIS REVEALS, QUANTUM-CHEMICAL CALCULATIONS, SPECIES-DEPENDENT BINDING, DRUG-BINDING, CRYSTAL-STRUCTURE, STRUCTURAL BASIS, ENERGY-TRANSFER, FATTY-ACIDS, SPECTRAL PROPERTIES",

author = "Er, {Jun Cheng} and Tang, {Mui Kee} and Chia, {Chee Geng} and Huimin Liew and Marc Vendrell and Young-Tae Chang",

year = "2013",

doi = "10.1039/c3sc22166k",

language = "English",

volume = "4",

pages = "2168--2176",

journal = "Chemical Science",

issn = "2041-6539",

publisher = "Royal Society of Chemistry",

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T1 - MegaStokes BODIPY-triazoles as environmentally sensitive turn-on fluorescent dyes

AU - Er, Jun Cheng

AU - Tang, Mui Kee

AU - Chia, Chee Geng

AU - Liew, Huimin

AU - Vendrell, Marc

AU - Chang, Young-Tae

PY - 2013

Y1 - 2013

N2 - A novel class of triazole-derivatized BODIPY compounds have been synthesized on solid-phase by employing mild reaction conditions based on the copper-catalyzed azide-alkyne cycloaddition. The resulting BODIPY-triazoles exhibited MegaStokes shifts (up to 160 nm) and remarkable environmentally sensitive quantum yield increments that asserted their potential as turn-on fluorescent sensors. Out of a library of 120 compounds, we identified BDC-9 as a fluorescent chemosensor with high sensitivity and remarkable species-selectivity towards human serum albumin. These results validate MegaStokes BODIPY dyes as new fluorophores for the development of environmentally sensitive fluorescent probes.

AB - A novel class of triazole-derivatized BODIPY compounds have been synthesized on solid-phase by employing mild reaction conditions based on the copper-catalyzed azide-alkyne cycloaddition. The resulting BODIPY-triazoles exhibited MegaStokes shifts (up to 160 nm) and remarkable environmentally sensitive quantum yield increments that asserted their potential as turn-on fluorescent sensors. Out of a library of 120 compounds, we identified BDC-9 as a fluorescent chemosensor with high sensitivity and remarkable species-selectivity towards human serum albumin. These results validate MegaStokes BODIPY dyes as new fluorophores for the development of environmentally sensitive fluorescent probes.

KW - HUMAN-SERUM-ALBUMIN

KW - CRYSTALLOGRAPHIC ANALYSIS REVEALS

KW - QUANTUM-CHEMICAL CALCULATIONS

KW - SPECIES-DEPENDENT BINDING

KW - DRUG-BINDING

KW - CRYSTAL-STRUCTURE

KW - STRUCTURAL BASIS

KW - ENERGY-TRANSFER

KW - FATTY-ACIDS

KW - SPECTRAL PROPERTIES

U2 - 10.1039/c3sc22166k

DO - 10.1039/c3sc22166k

M3 - Article

SN - 2041-6539

VL - 4

SP - 2168

EP - 2176

JO - Chemical Science

JF - Chemical Science

IS - 5

ER -

MegaStokes BODIPY-triazoles as environmentally sensitive turn-on fluorescent dyes

Abstract

Keywords / Materials (for Non-textual outputs)

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