Gated Electron Sharing Within Dynamic Naphthalene Diimide-Based Oligorotaxanes

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...

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Bibliographic Details
Published in:Angewandte Chemie 2014-04, Vol.126 (17), p.4531-4538
Main Authors: Avestro, Alyssa-Jennifer, 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
Format: Article
Language:eng ; ger
Subjects:
Charge transport
Chemistry
Diimide
Dynamics
Electronics
Elektronentransport
Inspection
Mechanisch verzahnte Moleküle
Naphthalene
Nondestructive testing
Radikalanionen
Selbstorganisation
Self assembly
Stacks
Templatsynthesen
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Summary: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. Seite an Seite: π‐Stapel aus [24]Krone‐8‐Derivaten von Naphthalindiimid (NDI) bilden sich dynamisch und selbstorganisiert an Templaten mit (CH2CH2NH2+CH2)‐Wiederholungseinheiten. So entstehen Oligorotaxane spezifischer Länge mit elektronischer Kommunikation über die parallel ausgerichteten π‐Oberflächen. Cyclovoltammetrie und EPR/ENDOR‐Spektroskopie zeigen, dass Elektronen in linearen Anordnungen aus einer bis vier NDI‐Einheiten geteilt werden.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201309680