Twelve-armed hexaphenylbenzene-based giant supramolecular framework for entrapping guest molecules

Title Twelve-armed hexaphenylbenzene-based giant supramolecular framework for entrapping guest molecules
Publication TypeJournal Article
Year of Publication2018
AuthorsMadhu, S, Gonnade, RG, Das, T, Vanka, K, Sanjayan, GJ
JournalChemPlusChem
Volume83
Issue11
Pagination1032-1037
Date PublishedNOV
Type of ArticleArticle
ISSN 2192-6506
Abstract

Host-guest chemistry is a functional model in supramolecular chemistry for understanding specific process occurring in biological systems. Herein, we describe a rationally designed giant multiarmed hexaphenylbenzene (HPB)-based supramolecular frameworks which encapsulate a variety of guest molecules in the voids of their crystal lattice through the cooperative interplay of multivalency, noncovalent forces and backbone rigidity. In this connection, pseudo-axially substituted twelve-armed hexaphenylbenzene was synthesized and its molecular entrapping nature was studied by varying number of H-bond donor-acceptor sites in the arms. The per-methyl esterified HPB acted as a cavitand to include nonpolar and polar aprotic guests in its crystal structure via C-H center dot center dot center dot pi, C-H center dot center dot center dot O and C-H center dot center dot center dot N interactions. The corresponding amidated HPB showed unprecedented inclusion of ammonia and segregation of the guest molecules according to their polarity in the lattice. Furthermore, this molecular entrapping system has been used to obtain the crystal structure of a hitherto unproven 2-azaallenium intermediate, which had been proposed to be involved in aminomethylation of activated arenes.

DOI10.1002/cplu.201800478
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.205

Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry
Physical and Materials Chemistry

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