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Thymine functionalised porphyrins, synthesis and heteromolecular surface-based self-assembly

Slater, Anna G.; Hu, Ya; Yang, Lixu; Argent, Stephen P.; Lewis, William; Blunt, Matthew O.; Champness, Neil R.

Authors

Anna G. Slater

Ya Hu

Lixu Yang

Stephen P. Argent

William Lewis

Matthew O. Blunt

Neil R. Champness



Abstract

The synthesis and surface-based self-assembly of thymine-functionalised porphyrins is described. Reaction of 1-formylphenyl-3-benzoyl-thymine with suitable pyrollic species leads to the formation of tetra-(phenylthymine)porphyrin (tetra-TP) or mono-thymine-tri-(3,5-di-tert-butylphenyl)porphyrin (mono-TP). Single crystal X-ray diffraction studies demonstrate the self-association of mono-TP in the solid state through thymine…thymine hydrogen-bonding interactions but in solution this interaction (Kd = 6.1 ± 3.0 M-1) is relatively weak in comparison to the heteromolecular interaction between mono-TP and 9-propyladenine (K = 91.8 ± 20.5 M-1). STM studies of the tetratopic hydrogen-bonding tecton, tetra-TP, deposited on an HOPG substrate reveal the formation of an almost perfectly square self-assembled lattice through thymine…thymine hydrogen-bonding. Co-deposition of tetra-TP with 9-propyladenine leads to the adoption of preferable thymine…adenine interactions leading to the formation of a heteromolecular tetra-TP…9-propyladenine hydrogen bonded array including both Watson-Crick thymine…adenine interactions and adenine…adenine hydrogen-bonding. The studies demonstrate a pathway for the self-assembly of tetratopic hydrogen-bonding tectons and the use of preferential heteromolecular thymine…adenine interactions for the disruption of the homomolecular tetra-TP array. Studies of the self-assembly of tetra-TP and 9-propyladenine demonstrate a strong dependence on overall concentration and molar ratio of components indicating the importance of kinetic effects in surface self-assembly processes.

Citation

Slater, A. G., Hu, Y., Yang, L., Argent, S. P., Lewis, W., Blunt, M. O., & Champness, N. R. (in press). Thymine functionalised porphyrins, synthesis and heteromolecular surface-based self-assembly. RSC Advances, 6, https://doi.org/10.1039/C4SC03531C

Journal Article Type Article
Acceptance Date Dec 11, 2014
Online Publication Date Dec 11, 2014
Deposit Date Aug 22, 2016
Publicly Available Date Aug 22, 2016
Journal Chemical Science
Print ISSN 2046-2069
Electronic ISSN 2046-2069
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 6
DOI https://doi.org/10.1039/C4SC03531C
Public URL http://eprints.nottingham.ac.uk/id/eprint/35948
Publisher URL http://pubs.rsc.org/en/Content/ArticleLanding/2015/SC/C4SC03531C#!divAbstract
Copyright Statement Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0





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