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A Molecular Plug−Socket Connector

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A monocationic plug−socket connector that is composed, at the molecular level, of threecomponents, (1) a secondary dialkylammonium center (CH2NH2+CH2), which can play the role of a plugtoward 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 dicationicplug, was synthesized and displays the ability to act as a plug−socket connector. The fluorescent signalchanges associated with the 1,5-dioxynaphthalene unit of its BN36C10 portion were monitored to investigatethe association of this plug−socket connector with the complementary socket and plug compounds. Theresults indicate that (1) the CH2NH2+CH2 part of the molecular connector can thread DB24C8 in a trivialmanner and (2) the BN36C10 ring of the connector can be threaded by a 1,1‘-dioctyl-4,4‘-bipyridinium iononly after the CH2NH2+CH2 site is occupied by a DB24C8 ring. The two connections of the three-componentassembly are shown to be controlled reversibly by acid/base and red/ox external inputs, respectively. Theresults obtained represent a key step for the design and construction of a self-assembling supramolecularsystem in which the molecular electron source can be connected to the molecular electron drain by amolecular elongation cable.

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