Bicyclic 1,3a,6a-Triazapentalene Chromophores: Synthesis, Spectroscopy and Their Use as Fluorescent Sensors and Probes
The 1,3a,6a-triazapentalene (TAP) is an aromatic heterocyclic fluorescent dye with interesting features such as its small size, large Stokes shift, solvatochromism, and emission wavelengths that are spread across the visible spectrum. TAPs have been synthesized via different synthetic strategies inv...
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doaj-7e179a8aae8541898f3dfd44320a5d582021-01-16T00:04:20ZengMDPI AGChemosensors2227-90402021-01-019161610.3390/chemosensors9010016Bicyclic 1,3a,6a-Triazapentalene Chromophores: Synthesis, Spectroscopy and Their Use as Fluorescent Sensors and ProbesYingchun Wang0Tomas Opsomer1Wim Dehaen2Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Heverlee, BelgiumMolecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Heverlee, BelgiumMolecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Heverlee, BelgiumThe 1,3a,6a-triazapentalene (TAP) is an aromatic heterocyclic fluorescent dye with interesting features such as its small size, large Stokes shift, solvatochromism, and emission wavelengths that are spread across the visible spectrum. TAPs have been synthesized via different synthetic strategies involving click−cyclization−aromatization domino reactions, gold-catalyzed cyclization of propargyl triazoles or triazolization of acetophenones. As a result, TAPs with diverse substitution patterns were obtained, showing varying fluorescence properties. Based on these properties, several TAPs have been selected and studied as fluorescent imaging probes in living cells and as sensors. This mini review provides an overview of the research on the bicyclic TAPs and does not comment on the literature about benzo or otherwise fused systems. The synthetic methodologies for the preparation of TAPs, the substituent effects on the fluorescence properties, and the behavior of the TAP core as an element of biological imaging probes and sensors are discussed.https://www.mdpi.com/2227-9040/9/1/161,3a,6a-triazapentalenesynthetic methodsfluorescence propertiesfluorescent imaging probesfluorescent sensorsliving cells |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Yingchun Wang Tomas Opsomer Wim Dehaen |
spellingShingle |
Yingchun Wang Tomas Opsomer Wim Dehaen Bicyclic 1,3a,6a-Triazapentalene Chromophores: Synthesis, Spectroscopy and Their Use as Fluorescent Sensors and Probes Chemosensors 1,3a,6a-triazapentalene synthetic methods fluorescence properties fluorescent imaging probes fluorescent sensors living cells |
author_facet |
Yingchun Wang Tomas Opsomer Wim Dehaen |
author_sort |
Yingchun Wang |
title |
Bicyclic 1,3a,6a-Triazapentalene Chromophores: Synthesis, Spectroscopy and Their Use as Fluorescent Sensors and Probes |
title_short |
Bicyclic 1,3a,6a-Triazapentalene Chromophores: Synthesis, Spectroscopy and Their Use as Fluorescent Sensors and Probes |
title_full |
Bicyclic 1,3a,6a-Triazapentalene Chromophores: Synthesis, Spectroscopy and Their Use as Fluorescent Sensors and Probes |
title_fullStr |
Bicyclic 1,3a,6a-Triazapentalene Chromophores: Synthesis, Spectroscopy and Their Use as Fluorescent Sensors and Probes |
title_full_unstemmed |
Bicyclic 1,3a,6a-Triazapentalene Chromophores: Synthesis, Spectroscopy and Their Use as Fluorescent Sensors and Probes |
title_sort |
bicyclic 1,3a,6a-triazapentalene chromophores: synthesis, spectroscopy and their use as fluorescent sensors and probes |
publisher |
MDPI AG |
series |
Chemosensors |
issn |
2227-9040 |
publishDate |
2021-01-01 |
description |
The 1,3a,6a-triazapentalene (TAP) is an aromatic heterocyclic fluorescent dye with interesting features such as its small size, large Stokes shift, solvatochromism, and emission wavelengths that are spread across the visible spectrum. TAPs have been synthesized via different synthetic strategies involving click−cyclization−aromatization domino reactions, gold-catalyzed cyclization of propargyl triazoles or triazolization of acetophenones. As a result, TAPs with diverse substitution patterns were obtained, showing varying fluorescence properties. Based on these properties, several TAPs have been selected and studied as fluorescent imaging probes in living cells and as sensors. This mini review provides an overview of the research on the bicyclic TAPs and does not comment on the literature about benzo or otherwise fused systems. The synthetic methodologies for the preparation of TAPs, the substituent effects on the fluorescence properties, and the behavior of the TAP core as an element of biological imaging probes and sensors are discussed. |
topic |
1,3a,6a-triazapentalene synthetic methods fluorescence properties fluorescent imaging probes fluorescent sensors living cells |
url |
https://www.mdpi.com/2227-9040/9/1/16 |
work_keys_str_mv |
AT yingchunwang bicyclic13a6atriazapentalenechromophoressynthesisspectroscopyandtheiruseasfluorescentsensorsandprobes AT tomasopsomer bicyclic13a6atriazapentalenechromophoressynthesisspectroscopyandtheiruseasfluorescentsensorsandprobes AT wimdehaen bicyclic13a6atriazapentalenechromophoressynthesisspectroscopyandtheiruseasfluorescentsensorsandprobes |
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