title: A molecular plug-socket connector.
abstract: A monocationic plug-socket connector that is composed, at the molecular level, of three components, (1) a secondary dialkylammonium center (CH2NH2+CH2), which can play the role of a plug toward dibenzo[24]crown-8 (DB24C8), (2) a rigid and conducting biphenyl spacer, and (3) 1,4-benzo-1,5-naphtho[36]crown-10 (BN36C10), capable of playing the role of a socket toward a 4,4'-bipyridinium dicationic plug, was synthesized and displays the ability to act as a plug-socket connector. The fluorescent signal changes associated with the 1,5-dioxynaphthalene unit of its BN36C10 portion were monitored to investigate the association of this plug-socket connector with the complementary socket and plug compounds. The results indicate that (1) the CH2NH2+CH2 part of the molecular connector can thread DB24C8 in a trivial manner and (2) the BN36C10 ring of the connector can be threaded by a 1,1'-dioctyl-4,4'-bipyridinium ion only after the CH2NH2+CH2 site is occupied by a DB24C8 ring. The two connections of the three-component assembly are shown to be controlled reversibly by acid/base and red/ox external inputs, respectively. The results obtained represent a key step for the design and construction of a self-assembling supramolecular system in which the molecular electron source can be connected to the molecular electron drain by a molecular elongation cable.
authors: Dipartimento di Chimica Giacomo Ciamician, Università di Bologna, via Selmi 2, I-40126 Bologna, Italy.
authors: Guillaume
authors: G
authors: Rogez
authors: Belén Ferrer
authors: BF
authors: Ribera
authors: Alberto
authors: A
authors: Credi
authors: Roberto
authors: R
authors: Ballardini
authors: Maria Teresa
authors: MT
authors: Gandolfi
authors: Vincenzo
authors: V
authors: Balzani
authors: Yi
authors: Y
authors: Liu
authors: Brian H
authors: BH
authors: Northrop
authors: J Fraser
authors: JF
authors: Stoddart