Emissive photoconversion products of an amino-triangulenium dye

Zhiyu Liao; Sidsel Ammitzbøll Bogh; Marco Santella; Christian Rein; Thomas Just Sørensen; Bo Wegge Laursen; Tom André Jos Vosch

doi:10.1021/acs.jpca.6b03134

Emissive photoconversion products of an amino-triangulenium dye

Zhiyu Liao, Sidsel Ammitzbøll Bogh, Marco Santella, Christian Rein, Thomas Just Sørensen, Bo Wegge Laursen, Tom André Jos Vosch

Department of Chemistry

3 Citations (Scopus)

Abstract

Upon prolonged exposure to intense blue light, the tris(diethylamino)-trioxatriangulenium (A₃-TOTA⁺) fluorophore can undergo a photochemical reaction to form either a blue-shifted or a red-shifted fluorescent photoproduct. The formation of the latter depends on the amount of oxygen present during the photoconversion. The A₃-TOTA⁺ fluorophore is structurally similar to rhodamine, with peripheral amino groups on a cationic aromatic system. The photoconversion products were identified by UV-vis absorption and steady-state and time-resolved fluorescence spectroscopy, and further characterized by HPLC, LC-MS, and ¹H NMR. Two reaction pathways were identified: a dealkylation reaction and an oxidation leading to formation of one or more amide groups on the peripheral donor groups. The photoconversion is controlled by the experimental conditions, in particular the presence of oxygen and water, and the choice of solvent. The results highlight the need to characterize the formation of fluorescent photoproducts of commonly used fluorescent probes, since these could give rise to false positives in multicolor/multilabel imaging, colocalization studies, and FRET based assays. Finally, an improved understanding of the photochemical reaction leading to bleaching of fluorescent dyes can lead to the creation of specific probes for fluorescence based monitoring of chemical reactions.

Original language	English
Journal	The Journal of Physical Chemistry Part A
Volume	120
Issue number	20
Pages (from-to)	3554–3561
Number of pages	8
ISSN	1089-5639
DOIs	https://doi.org/10.1021/acs.jpca.6b03134
Publication status	Published - 26 May 2016

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@article{45821e6e3bfb4a47932045b4510f0488,

title = "Emissive photoconversion products of an amino-triangulenium dye",

abstract = "Upon prolonged exposure to intense blue light, the tris(diethylamino)-trioxatriangulenium (A3-TOTA+) fluorophore can undergo a photochemical reaction to form either a blue-shifted or a red-shifted fluorescent photoproduct. The formation of the latter depends on the amount of oxygen present during the photoconversion. The A3-TOTA+ fluorophore is structurally similar to rhodamine, with peripheral amino groups on a cationic aromatic system. The photoconversion products were identified by UV-vis absorption and steady-state and time-resolved fluorescence spectroscopy, and further characterized by HPLC, LC-MS, and 1H NMR. Two reaction pathways were identified: a dealkylation reaction and an oxidation leading to formation of one or more amide groups on the peripheral donor groups. The photoconversion is controlled by the experimental conditions, in particular the presence of oxygen and water, and the choice of solvent. The results highlight the need to characterize the formation of fluorescent photoproducts of commonly used fluorescent probes, since these could give rise to false positives in multicolor/multilabel imaging, colocalization studies, and FRET based assays. Finally, an improved understanding of the photochemical reaction leading to bleaching of fluorescent dyes can lead to the creation of specific probes for fluorescence based monitoring of chemical reactions.",

author = "Zhiyu Liao and Bogh, {Sidsel Ammitzb{\o}ll} and Marco Santella and Christian Rein and S{\o}rensen, {Thomas Just} and Laursen, {Bo Wegge} and Vosch, {Tom Andr{\'e} Jos}",

year = "2016",

month = may,

day = "26",

doi = "10.1021/acs.jpca.6b03134",

language = "English",

volume = "120",

pages = "3554–3561",

journal = "Journal of Physical Chemistry Part A: Molecules, Spectroscopy, Kinetics, Environment and General Theory",

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T1 - Emissive photoconversion products of an amino-triangulenium dye

AU - Liao, Zhiyu

AU - Bogh, Sidsel Ammitzbøll

AU - Santella, Marco

AU - Rein, Christian

AU - Sørensen, Thomas Just

AU - Laursen, Bo Wegge

AU - Vosch, Tom André Jos

PY - 2016/5/26

Y1 - 2016/5/26

N2 - Upon prolonged exposure to intense blue light, the tris(diethylamino)-trioxatriangulenium (A3-TOTA+) fluorophore can undergo a photochemical reaction to form either a blue-shifted or a red-shifted fluorescent photoproduct. The formation of the latter depends on the amount of oxygen present during the photoconversion. The A3-TOTA+ fluorophore is structurally similar to rhodamine, with peripheral amino groups on a cationic aromatic system. The photoconversion products were identified by UV-vis absorption and steady-state and time-resolved fluorescence spectroscopy, and further characterized by HPLC, LC-MS, and 1H NMR. Two reaction pathways were identified: a dealkylation reaction and an oxidation leading to formation of one or more amide groups on the peripheral donor groups. The photoconversion is controlled by the experimental conditions, in particular the presence of oxygen and water, and the choice of solvent. The results highlight the need to characterize the formation of fluorescent photoproducts of commonly used fluorescent probes, since these could give rise to false positives in multicolor/multilabel imaging, colocalization studies, and FRET based assays. Finally, an improved understanding of the photochemical reaction leading to bleaching of fluorescent dyes can lead to the creation of specific probes for fluorescence based monitoring of chemical reactions.

AB - Upon prolonged exposure to intense blue light, the tris(diethylamino)-trioxatriangulenium (A3-TOTA+) fluorophore can undergo a photochemical reaction to form either a blue-shifted or a red-shifted fluorescent photoproduct. The formation of the latter depends on the amount of oxygen present during the photoconversion. The A3-TOTA+ fluorophore is structurally similar to rhodamine, with peripheral amino groups on a cationic aromatic system. The photoconversion products were identified by UV-vis absorption and steady-state and time-resolved fluorescence spectroscopy, and further characterized by HPLC, LC-MS, and 1H NMR. Two reaction pathways were identified: a dealkylation reaction and an oxidation leading to formation of one or more amide groups on the peripheral donor groups. The photoconversion is controlled by the experimental conditions, in particular the presence of oxygen and water, and the choice of solvent. The results highlight the need to characterize the formation of fluorescent photoproducts of commonly used fluorescent probes, since these could give rise to false positives in multicolor/multilabel imaging, colocalization studies, and FRET based assays. Finally, an improved understanding of the photochemical reaction leading to bleaching of fluorescent dyes can lead to the creation of specific probes for fluorescence based monitoring of chemical reactions.

U2 - 10.1021/acs.jpca.6b03134

DO - 10.1021/acs.jpca.6b03134

M3 - Journal article

C2 - 27149340

SN - 1089-5639

VL - 120

SP - 3554

EP - 3561

JO - Journal of Physical Chemistry Part A: Molecules, Spectroscopy, Kinetics, Environment and General Theory

JF - Journal of Physical Chemistry Part A: Molecules, Spectroscopy, Kinetics, Environment and General Theory

IS - 20

ER -

Emissive photoconversion products of an amino-triangulenium dye

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