Synthesis of pH-activatable red fluorescent BODIPY dyes with distinct functionalities

Sascha Hoogendoorn; Annet E.M. Blom; Lianne I. Willems; Gijsbert A. Van Der Marel; Herman S. Overkleeft

doi:10.1021/ol202379w

Synthesis of pH-activatable red fluorescent BODIPY dyes with distinct functionalities

Sascha Hoogendoorn, Annet E.M. Blom, Lianne I. Willems, Gijsbert A. Van Der Marel, Herman S. Overkleeft^*

^*Corresponding author for this work

Chemistry

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

Abstract

A series of tunable pH-dependent BODIPY dyes were synthesized and further functionalized in a Knoevenagel condensation reaction with various aldehydes. In this fashion, monofunctional dyes containing an alkyne, azide, or carboxylic acid (masked as its methyl ester) as ligation sites as well as asymmetrical bifunctional dyes were obtained, without compromising their pH-dependency. In addition, fluorescence excitation and emission maxima for these dyes were shown to be significantly red-shifted in comparison to their tetramethyl precursors.

Original language	English
Pages (from-to)	5656-5659
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	20
DOIs	https://doi.org/10.1021/ol202379w
Publication status	Published - 21 Oct 2011

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10.1021/ol202379w

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abstract = "A series of tunable pH-dependent BODIPY dyes were synthesized and further functionalized in a Knoevenagel condensation reaction with various aldehydes. In this fashion, monofunctional dyes containing an alkyne, azide, or carboxylic acid (masked as its methyl ester) as ligation sites as well as asymmetrical bifunctional dyes were obtained, without compromising their pH-dependency. In addition, fluorescence excitation and emission maxima for these dyes were shown to be significantly red-shifted in comparison to their tetramethyl precursors.",

author = "Sascha Hoogendoorn and Blom, {Annet E.M.} and Willems, {Lianne I.} and {Van Der Marel}, {Gijsbert A.} and Overkleeft, {Herman S.}",

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AU - Hoogendoorn, Sascha

AU - Blom, Annet E.M.

AU - Willems, Lianne I.

AU - Van Der Marel, Gijsbert A.

AU - Overkleeft, Herman S.

PY - 2011/10/21

Y1 - 2011/10/21

N2 - A series of tunable pH-dependent BODIPY dyes were synthesized and further functionalized in a Knoevenagel condensation reaction with various aldehydes. In this fashion, monofunctional dyes containing an alkyne, azide, or carboxylic acid (masked as its methyl ester) as ligation sites as well as asymmetrical bifunctional dyes were obtained, without compromising their pH-dependency. In addition, fluorescence excitation and emission maxima for these dyes were shown to be significantly red-shifted in comparison to their tetramethyl precursors.

AB - A series of tunable pH-dependent BODIPY dyes were synthesized and further functionalized in a Knoevenagel condensation reaction with various aldehydes. In this fashion, monofunctional dyes containing an alkyne, azide, or carboxylic acid (masked as its methyl ester) as ligation sites as well as asymmetrical bifunctional dyes were obtained, without compromising their pH-dependency. In addition, fluorescence excitation and emission maxima for these dyes were shown to be significantly red-shifted in comparison to their tetramethyl precursors.

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U2 - 10.1021/ol202379w

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 20

ER -

Synthesis of pH-activatable red fluorescent BODIPY dyes with distinct functionalities

Abstract

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