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Gated Electron Sharing Within Dynamic Naphthalene Diimide‐Based Oligorotaxanes
Author(s) -
Avestro AlyssaJennifer,
Gardner Daniel M.,
Vermeulen Nicolaas A.,
Wilson Eleanor A.,
Schneebeli Severin T.,
Whalley Adam C.,
Belowich Matthew E.,
Carmieli Raanan,
Wasielewski Michael R.,
Stoddart J. Fraser
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201309680
Subject(s) - diimide , cyclic voltammetry , electron , chemistry , redox , nanotechnology , electron transport chain , electron transfer , chemical physics , materials science , electrochemistry , photochemistry , physics , molecule , electrode , organic chemistry , biochemistry , perylene , quantum mechanics
The controlled self‐assembly of well‐defined and spatially ordered π‐systems has attracted considerable interest because of their potential applications in organic electronics. An important contemporary pursuit relates to the investigation of charge transport across noncovalently coupled components in a stepwise fashion. Dynamic oligorotaxanes, prepared by template‐directed methods, provide a scaffold for directing the construction of monodisperse one‐dimensional assemblies in which the functional units communicate electronically through‐space by way of π‐orbital interactions. Reported herein is a series of oligorotaxanes containing one, two, three and four naphthalene diimide (NDI) redox‐active units, which have been shown by cyclic voltammetry, and by EPR and ENDOR spectroscopies, to share electrons across the NDI stacks. Thermally driven motions between the neighboring NDI units in the oligorotaxanes influence the passage of electrons through the NDI stacks in a manner reminiscent of the conformationally gated charge transfer observed in DNA.