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End-to-end communication in a linear supermolecule with a BOPHY centre and: N,N-dimethylanilino-based terminals

Lookup NU author(s): Owen Woodford, Patrycja Stachelek, Dr Raymond Ziessel, Nawaf Algoazy, Dr Julian Knight, Emeritus Professor Anthony Harriman

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This is the authors' accepted manuscript of an article that has been published in its final definitive form by Royal Society of Chemistry, 2018.

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Abstract

© 2018 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique. The recently introduced BOPHY (i.e., symmetrical bis(pyrrole-BF2)) chromophore is a highly attractive building block for constructing linear molecules with extended π-conjugation running along the molecular backbone. In order to assess the level of electronic communication between the terminal groups in this type of supermolecule, we have examined selective protonation and oxidation of the bis-(N,N-dimethylanilino-styryl) derivative. The amino N atoms are separated by 22.6 Å via a conjugated pathway but there is no indication of through-bond electronic coupling. Instead, the disparate pKa values and also reduction potentials found for one-electron oxidation of each aniline group are well explained in terms of very long-range electrostatic interactions. It is necessary, however, to allow for the effects of ion-pairing. As an interesting aside, it is shown that protonation can be achieved in a cast PMMA film by using a suitable photo-acid generator.


Publication metadata

Author(s): Woodford OJ, Stachelek P, Ziessel R, Algoazy N, Knight JG, Harriman A

Publication type: Article

Publication status: Published

Journal: New Journal of Chemistry

Year: 2018

Volume: 42

Issue: 7

Pages: 4835-4842

Print publication date: 07/04/2018

Online publication date: 13/02/2018

Acceptance date: 12/02/2018

Date deposited: 11/05/2018

ISSN (print): 1144-0546

ISSN (electronic): 1369-9261

Publisher: Royal Society of Chemistry

URL: https://doi.org/10.1039/c7nj04654e

DOI: 10.1039/c7nj04654e


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