pH‐Controlled Molecular Switches and the Substrate‐Directed Self‐Assembly of Molecular Capsules with a Calix[4]pyrrole Derivative | Zendy

Cafeo Grazia | Zendy; Kohnke Franz H. | Zendy; Valenti Luca | Zendy; White Andrew J. P. | Zendy

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pH‐Controlled Molecular Switches and the Substrate‐Directed Self‐Assembly of Molecular Capsules with a Calix[4]pyrrole Derivative

Author(s) -

Cafeo Grazia,

Kohnke Franz H.,

Valenti Luca,

White Andrew J. P.

Publication year - 2008

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.200800819

Subject(s) - pyrrole , chemistry , calixarene , molecule , substrate (aquarium) , solid state , stereochemistry , derivative (finance) , molecular recognition , crystallography , polymer chemistry , organic chemistry , oceanography , financial economics , economics , geology

10α,20α‐Bis(4‐nitrophenyl)calix[4]pyrrole ( 1 ) forms 1:1 complexes with anions of selected aromatic hydroxy acids in which the host orientation within the guest is controlled by a change in the pH value. Some bis‐anionic guests, including those obtained from 4‐hydroxybenzoic acid, 1,4‐ and 1,3‐benzenedicarboxylic acids, induce the self‐assembly of molecular capsules involving two molecules of the receptor. 1 H NMR data and solid‐state structures of the 1:1 complex of 1 with p ‐C 6 H 4 (COOH)(COO − ) + NMe 4 and the 2:1 capsule [( 1 ) 2 m ‐C 6 H 4 (COO − ) 2 ( + NMe 4 ) 2 ] provide structural details in solution and in the solid state.

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