NDLI: Pyrrolyl-, 2-(2-thienyl)pyrrolyl- and 2,5-bis(2-thienyl)pyrrolyl-nucleosides: synthesis, molecular and electronic structure, and redox behaviour of C5-thymidine derivatives

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Pyrrolyl-, 2-(2-thienyl)pyrrolyl- and 2,5-bis(2-thienyl)pyrrolyl-nucleosides: synthesis, molecular and electronic structure, and redox behaviour of C5-thymidine derivatives

Content Provider	Royal Society of Chemistry (RSC)
Author	Galindo, Miguel A. Clegg, William Pike, Andrew R. Horrocks, Benjamin R. Harrington, Ross W. Hannant, Jennifer Houlton, Andrew
Copyright Year	2011
Abstract	A series of modified nucleosides based on thymidine have been prepared by Pd-catalysed cross-coupling between N-alkyl-alkynyl functionalised pyrrolyl- (py), 2-(2-thienyl)pyrrolyl- (tp) or 2,5-bis(2-thienyl)pyrrolyl (tpt) groups with 5-iodo-2′-deoxyuridine. The length of the alkyl chain linking the nucleoside and pyrrolyl-containing unit, N(CH2)nCC-nucleoside (where n = 1–3) was also varied. The compounds have been characterised by 1H NMR, ES-MS, UV–vis, cyclic voltammetry (CV) and, in some cases, single-crystal X-ray diffraction. Cyclic voltammetry studies demonstrated that all the py-, tp- and tpt-alkynyl derivatives 1–7 can be electrochemically polymerised to form conductive materials. It was found that increasing the N-alkyl chain length in these cases resulted in only minor changes in the oxidation potential. The same behaviour was observed for the tp- and tpt-modified nucleosides 9–12; however, the py-derivative, 8, produced a poorly conducting material. DFT calculations on the one-electron oxidised cation of the modified nucleosides bearing tp or tpt showed that spin density is located on the pyrrolyl and thienyl units in all cases and that the coplanarity of adjacent rings increases upon oxidation. In contrast, in the corresponding pyrrolyl cases the spin density is distributed over the whole molecule, suggesting that polymerisation does not occur solely at the pyrrolyl-Cα position and the conjugation is interrupted.
Starting Page	1555
Ending Page	1564
Page Count	10
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	9
Issue Number	5
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c0ob00466a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Cyclic voltammetry X-ray crystallography Tissue paper Deoxyuridine Alkyl Coplanarity Nucleoside Ion Thymidine Nuclear magnetic resonance
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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