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Updated: Jun 27, 2026

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
Published on: October 15, 2019
pH-Controlled molecular switches and the substrate-directed self-assembly of molecular capsules with a
Grazia Cafeo1, Franz H Kohnke, Luca Valenti
1Dipartimento di Chimica Organica e Biologica, Università di Messina, Salita Sperone 31, 98166 Messina, Italy.
Abstract:
10alpha,20alpha-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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