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

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Chemical Science Vol -5

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Chemical Science Vol -1

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

Content Provider	Royal Society of Chemistry (RSC)
Author	Champness, Neil R. Argent, Stephen P. Lewis, William Yang, Lixu Blunt, Matthew O. Hu, Ya Slater, Anna G.
Copyright Year	2015
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.
Starting Page	1562
Ending Page	1569
Page Count	8
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	6
Issue Number	2
Journal	Chemical Science
DOI	10.1039/c4sc03531c
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Subscribed
Subject Keyword	Crick Thymine Adenine Dissociation constant Watson Single crystal X-ray crystallography Self-assembly Porphyrin Tecton Group Correlation and dependence Crystal structure Hydrogen bond
Content Type	Text
Resource Type	Article
Subject	Chemistry

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Structure of stacked dimers of n-methylated watson–crick adenine–thymine base.

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Halogen- and hydrogen-bonding triazole-functionalised porphyrin-based receptors for anion recognition

Crystallographic evidence of Watson-Crick connectivity in the base pair of anionic adenine with thymine.

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

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