Lookup NU author(s): Owen Woodford,
Dr Raymond Ziessel,
Dr Julian Knight,
Emeritus Professor Anthony Harriman
This is the authors' accepted manuscript of an article that has been published in its final definitive form by Royal Society of Chemistry, 2018.
For re-use rights please refer to the publisher's terms and conditions.
© 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.
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
Print publication date: 07/04/2018
Online publication date: 13/02/2018
Acceptance date: 12/02/2018
ISSN (print): 1144-0546
ISSN (electronic): 1369-9261
Publisher: Royal Society of Chemistry
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