Molecular tectonics: tetracarboxythiacalix[4]arene derivatives as tectons for the formation of hydrogen-bonded networks

A series of thiacalix[4]arene derivatives blocked in the 1,3-alternate conformation and bearing four carboxylic acids have been designed and synthesized. These compounds, owing to the H-bond donor (OH moiety) and acceptor (C&z.dbd; O group) nature of the carboxylic acid moieties, behave as self-...

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Bibliographic Details
Published in:CrystEngComm 2016-01, Vol.18 (44), p.8622-8630
Main Authors: Ovsyannikov, A. S., Lang, M. N., Ferlay, S., Solovieva, S. E., Antipin, I. S., Konovalov, A. I., Kyritsakas, N., Hosseini, M. W.
Format: Article
Language:English
Subjects:
Carboxylates
Carboxylic acids
Chemical Sciences
Derivatives
Formations
Hydrogen bonding
Material chemistry
Networks
Organic chemistry
Self assembly
Transformations
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Summary:A series of thiacalix[4]arene derivatives blocked in the 1,3-alternate conformation and bearing four carboxylic acids have been designed and synthesized. These compounds, owing to the H-bond donor (OH moiety) and acceptor (C&z.dbd; O group) nature of the carboxylic acid moieties, behave as self-complementary tectons and lead to the formation of tubular 1D H-bonded networks in the crystalline phase. Upon deprotonation of the self-complementary neutral compounds, i.e. transformation of carboxylic acid moieties into carboxylates, anionic tectons are generated. Due to their propensity to form H-bonded networks in the presence of a dicationic H-bond donor tecton of the cyclic bis-amidinium type, designed to behave as a molecular staple interconnecting two carboxylates moieties, 1- and 2-D H-bonded networks are formed under self-assembly conditions.
ISSN:1466-8033
1466-8033
DOI:10.1039/C6CE02026G