Next Article in Journal
Lipase-Catalyzed Synthesis of Sucrose Monolaurate and Its Antibacterial Property and Mode of Action against Four Pathogenic Bacteria
Previous Article in Journal
Investigation of the Antifungal Activity and Mode of Action of Thymus vulgaris, Citrus limonum, Pelargonium graveolens, Cinnamomum cassia, Ocimum basilicum, and Eugenia caryophyllus Essential Oils
Article Menu
Issue 5 (May) cover image

Export Article

Open AccessArticle
Molecules 2018, 23(5), 1117; https://doi.org/10.3390/molecules23051117

Synthesis of Water-Soluble Amino Functionalized Multithiacalix[4]arene via Quaternization of Tertiary Amino Groups

A.M. Butlerov Chemistry Institute, Kazan Federal University, 420008 Kazan, Russia
*
Author to whom correspondence should be addressed.
Received: 27 April 2018 / Revised: 7 May 2018 / Accepted: 7 May 2018 / Published: 8 May 2018
(This article belongs to the Section Organic Chemistry)
Full-Text   |   PDF [4138 KB, uploaded 21 May 2018]   |  

Abstract

A convenient approach to the synthesis of multithiacalix[4]arene derivatives containing amino groups and phthalimide fragments by the formation of quaternary ammonium salts is presented. As the initial macrocycle for the synthesis of multithiacalix[4]arenes, a differently substituted p-tert-butylthiacalix[4]arene containing bromoacetamide and three phthalimide fragments was used in a 1,3-alternate conformation. The macrocycle in cone conformation containing the tertiary amino groups was found to be a convenient core for the multithiacalix[4]arene systems. Interaction of the core multithiacalix[4]arene with monobromoacetamide derivatives of p-tert-butylthiacalix[4]arene resulted in formation in high yields of pentakisthiacalix[4]arene containing quaternary ammonium and phthalimide fragments. The removal of phthalimide groups led to the formation of amino multithiacalix[4]arene in a good yield. Based on dynamic light scattering, it was shown that the synthesized amino multithiacalix[4]arene, with pronounced hydrophobic and hydrophilic fragments, formed dendrimer-like nanoparticles in water via direct supramolecular self-assembly. View Full-Text
Keywords: thiacalix[4]arene; receptor; aggregation; self-assembly; amino derivatives; nanoparticles; dendrimers; multithiacalix[4]arene thiacalix[4]arene; receptor; aggregation; self-assembly; amino derivatives; nanoparticles; dendrimers; multithiacalix[4]arene
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

Nosov, R.; Padnya, P.; Shurpik, D.; Stoikov, I. Synthesis of Water-Soluble Amino Functionalized Multithiacalix[4]arene via Quaternization of Tertiary Amino Groups. Molecules 2018, 23, 1117.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top