Design and syntheses of novel fluorescent organosilicon-based chemosensors through click silylation: detection of biogenic amines

A concise and useful synthesis of novel 1,2,3-triazole based silatrane (TBS)-scaffolds ( 2a–e ) in good yield from 1,2,3-triazole based triethoxysilane (TBTES)-linkers ( 1a–e ) is described. Click silylation of terminal alkynes with γ-azidopropyltriethoxysilane (AzPTES) was used for the synthesis of...

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Published inRSC advances Vol. 4; no. 69; pp. 36834 - 36844
Main Authors Singh, Gurjaspreet, Mangat, Satinderpal Singh, Sharma, Hemant, Singh, Jandeep, Arora, Aanchal, Singh Pannu, Ajay Pal, Singh, Narinder
Format Journal Article
LanguageEnglish
Published 01.01.2014
Subjects
Affinity
Alkynes
Amines
Chemoreceptors
Design engineering
Solvents
Synthesis
Terminals
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Summary:A concise and useful synthesis of novel 1,2,3-triazole based silatrane (TBS)-scaffolds ( 2a–e ) in good yield from 1,2,3-triazole based triethoxysilane (TBTES)-linkers ( 1a–e ) is described. Click silylation of terminal alkynes with γ-azidopropyltriethoxysilane (AzPTES) was used for the synthesis of TBTES-linkers ( 1a–e ). The synthesized TBS-scaffolds ( 2a–e ) were comprehensively characterized by 1 H and 13 C NMR, mass spectrometry and single X-ray crystallographic studies. The broad scope of these TBS-scaffolds towards biogenic amines is explored by the use of a CH 3 CN : H 2 O (98 : 2; v/v) solvent system. The receptor 2c and 2d shows high affinity towards spermine and histamine, respectively. To the best of our knowledge, the present investigation represents the first report on the use of organosilicon-based chemosensors for the recognition of biogenic amines.
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ISSN:2046-2069
2046-2069
DOI:10.1039/C4RA02270J