Self-assembly of chiral fluorescent nanoparticles based on water-soluble L-tryptophan derivatives of p-tert-butylthiacalix[4]arene

New water-soluble tetra-substituted derivatives of p-tert-butylthiacalix[4]arene containing fragments of L-tryptophan in cone and 1,3-alternate conformations were obtained. It was shown that the resulting compounds form stable, positively charged aggregates of 86–134 nm in diameter in water at a con...

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Main Authors:	Pavel L. Padnya, Irina A. Khripunova, Olga A. Mostovaya, Timur A. Mukhametzyanov, Vladimir G. Evtugyn, Vyacheslav V. Vorobev, Yuri N. Osin, Ivan I. Stoikov
Format:	Article
Language:	English
Published:	Beilstein-Institut 2017-09-01
Series:	Beilstein Journal of Nanotechnology
Subjects:	fluorescence nanoparticles self-assembly thiacalixarene tryptophan
Online Access:	https://doi.org/10.3762/bjnano.8.184

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spelling	doaj-be618f10a682430e821011804c268f702020-11-25T01:46:54ZengBeilstein-InstitutBeilstein Journal of Nanotechnology2190-42862017-09-01811825183510.3762/bjnano.8.1842190-4286-8-184Self-assembly of chiral fluorescent nanoparticles based on water-soluble L-tryptophan derivatives of p-tert-butylthiacalix[4]arenePavel L. Padnya0Irina A. Khripunova1Olga A. Mostovaya2Timur A. Mukhametzyanov3Vladimir G. Evtugyn4Vyacheslav V. Vorobev5Yuri N. Osin6Ivan I. Stoikov7Kazan Federal University, 420008 Kremlevskaya, 18, Kazan, Russian FederationKazan Federal University, 420008 Kremlevskaya, 18, Kazan, Russian FederationKazan Federal University, 420008 Kremlevskaya, 18, Kazan, Russian FederationKazan Federal University, 420008 Kremlevskaya, 18, Kazan, Russian FederationKazan Federal University, 420008 Kremlevskaya, 18, Kazan, Russian FederationKazan Federal University, 420008 Kremlevskaya, 18, Kazan, Russian FederationKazan Federal University, 420008 Kremlevskaya, 18, Kazan, Russian FederationKazan Federal University, 420008 Kremlevskaya, 18, Kazan, Russian FederationNew water-soluble tetra-substituted derivatives of p-tert-butylthiacalix[4]arene containing fragments of L-tryptophan in cone and 1,3-alternate conformations were obtained. It was shown that the resulting compounds form stable, positively charged aggregates of 86–134 nm in diameter in water at a concentration of 1 × 10−4 M as confirmed by dynamic light scattering, scanning electron microscopy and transmission electron microscopy. It was established that these aggregates are fluorescently active and chiral. A distinctive feature of the compounds is the pronounced dependence of their spectral (emission and chiroptical) properties on the polarity of the solvent and the length of the linker between the macrocyclic and fluorophore parts of the molecule.https://doi.org/10.3762/bjnano.8.184fluorescencenanoparticlesself-assemblythiacalixarenetryptophan
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Pavel L. Padnya Irina A. Khripunova Olga A. Mostovaya Timur A. Mukhametzyanov Vladimir G. Evtugyn Vyacheslav V. Vorobev Yuri N. Osin Ivan I. Stoikov
spellingShingle	Pavel L. Padnya Irina A. Khripunova Olga A. Mostovaya Timur A. Mukhametzyanov Vladimir G. Evtugyn Vyacheslav V. Vorobev Yuri N. Osin Ivan I. Stoikov Self-assembly of chiral fluorescent nanoparticles based on water-soluble L-tryptophan derivatives of p-tert-butylthiacalix[4]arene Beilstein Journal of Nanotechnology fluorescence nanoparticles self-assembly thiacalixarene tryptophan
author_facet	Pavel L. Padnya Irina A. Khripunova Olga A. Mostovaya Timur A. Mukhametzyanov Vladimir G. Evtugyn Vyacheslav V. Vorobev Yuri N. Osin Ivan I. Stoikov
author_sort	Pavel L. Padnya
title	Self-assembly of chiral fluorescent nanoparticles based on water-soluble L-tryptophan derivatives of p-tert-butylthiacalix[4]arene
title_short	Self-assembly of chiral fluorescent nanoparticles based on water-soluble L-tryptophan derivatives of p-tert-butylthiacalix[4]arene
title_full	Self-assembly of chiral fluorescent nanoparticles based on water-soluble L-tryptophan derivatives of p-tert-butylthiacalix[4]arene
title_fullStr	Self-assembly of chiral fluorescent nanoparticles based on water-soluble L-tryptophan derivatives of p-tert-butylthiacalix[4]arene
title_full_unstemmed	Self-assembly of chiral fluorescent nanoparticles based on water-soluble L-tryptophan derivatives of p-tert-butylthiacalix[4]arene
title_sort	self-assembly of chiral fluorescent nanoparticles based on water-soluble l-tryptophan derivatives of p-tert-butylthiacalix[4]arene
publisher	Beilstein-Institut
series	Beilstein Journal of Nanotechnology
issn	2190-4286
publishDate	2017-09-01
description	New water-soluble tetra-substituted derivatives of p-tert-butylthiacalix[4]arene containing fragments of L-tryptophan in cone and 1,3-alternate conformations were obtained. It was shown that the resulting compounds form stable, positively charged aggregates of 86–134 nm in diameter in water at a concentration of 1 × 10−4 M as confirmed by dynamic light scattering, scanning electron microscopy and transmission electron microscopy. It was established that these aggregates are fluorescently active and chiral. A distinctive feature of the compounds is the pronounced dependence of their spectral (emission and chiroptical) properties on the polarity of the solvent and the length of the linker between the macrocyclic and fluorophore parts of the molecule.
topic	fluorescence nanoparticles self-assembly thiacalixarene tryptophan
url	https://doi.org/10.3762/bjnano.8.184
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Self-assembly of chiral fluorescent nanoparticles based on water-soluble L-tryptophan derivatives of p-tert-butylthiacalix[4]arene

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