Regioselective SNAr reaction of the phenoxathiin-based thiacalixarene as a route to a novel macrocyclic skeleton

Author(s): Tomáš Landovský ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Václav Eigner ⁶ ^, ⁷ ^, ⁴ ^, ⁵ , Martin Babor ⁶ ^, ⁷ ^, ⁴ ^, ⁵ , Markéta Tichotová ⁸ ^, ⁷ ^, ⁴ ^, ⁵ , Hana Dvořáková ⁸ ^, ⁷ ^, ⁴ ^, ⁵ , Pavel Lhoták ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵

Publication date (Electronic): 2020

Journal: Chemical Communications

Publisher: Royal Society of Chemistry (RSC)

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Abstract

The formation of a novel type of macrocyclic skeleton possessing meta- and para-bridging units can be achieved by S _NAr cleavage of an easily accessible phenoxathiin-based thiacalix[4]arene.

Abstract

The sulfonyl analogue of phenoxathiin-based thiacalix[4]arene, easily accessible from the parent thiacalix[4]arene, reacts with sodium alkoxides to yield a cleaved product representing a novel type of macrocyclic skeleton with a quasi-calixarene structure. As shown by comparison with other derivatives, the internal strain imposed by the heterocyclic moiety is a driving force of this S _NAr reaction.

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Most cited references 23

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Thiacalixarenes.

Tetsutaro Hattori, Sotaro Miyano, Naoya Morohashi … (2006)

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Chemistry of Thiacalixarenes

Pavel Lhotak (2004)

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Recent developments of thiacalixarene based molecular motifs.

Rajesh Kumar, Yeon Ok Lee, Vandana Bhalla … (2014)

Thiacalixarenes, a subclass of "third generation" calixarenes, exhibit many interesting features such as enlarged ring size, facile chemical modification, and metal complexation due to the presence of bridging sulfur atoms. The thiacalixarene scaffold is a unique host with vast possibilities for functionalization not only at the upper and lower rim but also at the bridging sulfide groups. Modified thiacalixarenes have been used for many applications such as the detection and separation of biologically important cations, anions, and bio-analytes, mimicking molecular logic gates and devices, and synthesis of self-assembled coordination cages, multinuclear complexes, magnetic materials and luminescent materials. This review article summarizes recent developments in the derivatization methods of thiacalixarenes and their utilization in various applications.