Thymine functionalised porphyrins, synthesis and heteromolecular surface-based self-assembly
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 (mon...
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| Format: | Article |
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Royal Society of Chemistry
2014
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| Online Access: | https://eprints.nottingham.ac.uk/35948/ |
| _version_ | 1848795196243836928 |
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| author | Slater, Anna G. Hu, Ya Yang, Lixu Argent, Stephen P. Lewis, William Blunt, Matthew O. Champness, Neil R. |
| author_facet | Slater, Anna G. Hu, Ya Yang, Lixu Argent, Stephen P. Lewis, William Blunt, Matthew O. Champness, Neil R. |
| author_sort | Slater, Anna G. |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T19:28:14Z |
| format | Article |
| id | nottingham-35948 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T19:28:14Z |
| publishDate | 2014 |
| publisher | Royal Society of Chemistry |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-359482020-05-04T16:58:54Z https://eprints.nottingham.ac.uk/35948/ 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. 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. Royal Society of Chemistry 2014-12-11 Article PeerReviewed Slater, Anna G., Hu, Ya, Yang, Lixu, Argent, Stephen P., Lewis, William, Blunt, Matthew O. and Champness, Neil R. (2014) Thymine functionalised porphyrins, synthesis and heteromolecular surface-based self-assembly. Chemical Science, 6 . pp. 1562-1569. ISSN 2046-2069 http://pubs.rsc.org/en/Content/ArticleLanding/2015/SC/C4SC03531C#!divAbstract doi:10.1039/C4SC03531C doi:10.1039/C4SC03531C |
| spellingShingle | Slater, Anna G. Hu, Ya Yang, Lixu Argent, Stephen P. Lewis, William Blunt, Matthew O. Champness, Neil R. Thymine functionalised porphyrins, synthesis and heteromolecular surface-based self-assembly |
| title | Thymine functionalised porphyrins, synthesis and heteromolecular surface-based self-assembly |
| title_full | Thymine functionalised porphyrins, synthesis and heteromolecular surface-based self-assembly |
| title_fullStr | Thymine functionalised porphyrins, synthesis and heteromolecular surface-based self-assembly |
| title_full_unstemmed | Thymine functionalised porphyrins, synthesis and heteromolecular surface-based self-assembly |
| title_short | Thymine functionalised porphyrins, synthesis and heteromolecular surface-based self-assembly |
| title_sort | thymine functionalised porphyrins, synthesis and heteromolecular surface-based self-assembly |
| url | https://eprints.nottingham.ac.uk/35948/ https://eprints.nottingham.ac.uk/35948/ https://eprints.nottingham.ac.uk/35948/ |