The thermodynamics of the self-assembly of covalently linked oligomeric naphthalenediimides into helical organic nanotubes

Koujiro Tambara; John-Carl Olsen; David E. Hansen; G. Dan Pantoş

doi:10.1039/C3OB41761A

The thermodynamics of the self-assembly of covalently linked oligomeric naphthalenediimides into helical organic nanotubes†

Koujiro Tambara,^a John-Carl Olsen,^b David E. Hansen^c and G. Dan Pantoş*^d

* Corresponding authors

^a University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK
E-mail: kt287@cam.ac.uk
Tel: +44 (0)1223 336300

^b School of Sciences, Indiana University Kokomo, Kokomo, IN 46904, USA
E-mail: olsenj@iuk.edu
Tel: +1 (765) 455 9207

^c W.M. Keck Science Department of Claremont McKenna, Pitzer, and Scripps Colleges, 925 N. Mills Avenue, Claremont, CA 91711, USA
E-mail: dhansen@kecksci.claremont.edu
Tel: +1 (909) 607 2565

^d Department of Chemistry, University of Bath, Bath BA2 7AY, UK
E-mail: g.d.pantos@bath.ac.uk
Tel: +44 (0)1225 384376

Abstract

The mechanism and thermodynamic functions of the self-assembly of a family of covalently linked oligomeric naphthalenediimides (NDIs) were investigated through variable-temperature NMR and CD studies. The NDIs were shown to self-assemble into helical supramolecular nanotubes via an isodesmic polymerisation mechanism, and regardless of the oligomer length a surprising entropy–enthalpy compensation was observed.

This article is part of the themed collection: J400: Celebrating the 400th year of Japan-UK relations

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DOI: https://doi.org/10.1039/C3OB41761A
Article type: Paper
Submitted: 28 Aug 2013
Accepted: 13 Nov 2013
First published: 13 Nov 2013
This article is Open Access

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Org. Biomol. Chem., 2014,12, 607-614

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The thermodynamics of the self-assembly of covalently linked oligomeric naphthalenediimides into helical organic nanotubes

K. Tambara, J. Olsen, D. E. Hansen and G. D. Pantoş, Org. Biomol. Chem., 2014, 12, 607 DOI: 10.1039/C3OB41761A

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Organic & Biomolecular Chemistry

The thermodynamics of the self-assembly of covalently linked oligomeric naphthalenediimides into helical organic nanotubes†

Abstract

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The thermodynamics of the self-assembly of covalently linked oligomeric naphthalenediimides into helical organic nanotubes

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