Premium
Twelve‐Armed Hexaphenylbenzene‐Based Giant Supramolecular Framework for Entrapping Guest Molecules
Author(s) -
Madhu Suresh,
Gonnade Rajesh G.,
Das Tamal,
Vanka Kumar,
Sanjayan Gangadhar J.
Publication year - 2018
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201800478
Subject(s) - supramolecular chemistry , chemistry , cavitand , molecule , cucurbituril , self assembly , crystal structure , non covalent interactions , crystal engineering , crystallography , polymer chemistry , combinatorial chemistry , stereochemistry , hydrogen bond , organic chemistry
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⋅⋅⋅π, C−H⋅⋅⋅O and C−H⋅⋅⋅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.