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Solid phase and solution phase structural characterization of pyrene-based, T-shaped molecular dyads

Lookup NU author(s): Dr Donocadh Lydon, Dr Peiyi Li, Professor Andrew Benniston, Emeritus Professor William McFarlane, Dr Ross Harrington, Emeritus Professor Bill Clegg

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Abstract

Structural solid-phase and solution-phase properties of two pyrene-spiropyran molecular dyads are described. Each dyad comprises a 1,1′-[indole-4,6-diylbis(ethyne-2,1-diyl)]-bis(pyrene) backbone, with the bis(pyrene) and spiropyran units adopting a T-shaped arrangement. The strength of the Cspiro-O bond is altered by replacement of H by NO2 in the terminal aryl group of the spiropyran unit. X-ray crystal structure determinations carried out for two of the dyads (H and NO2) reveal the pyrene groups to be aligned anti to each other. The crystal packing diagrams are different; both contain pyrene π-stacked centro-symmetric dimers, but in one structure this is the total extent of the π stacking whereas the other structure has pyrene dimers interleaved to generate infinite parallel stacks. Detailed 1H NOE experiments are consistent with a solution-phase structure that differs markedly from the solid-state structure, and in which the pyrene groups are syn to one another but orientated away from the spiropyran group. © Wiley-VCH Verlag GmbH & Co. KGaA, 2007.


Publication metadata

Author(s): Lydon DP, Li P, Benniston AC, McFarlane W, Harrington RW, Clegg W

Publication type: Article

Publication status: Published

Journal: European Journal of Organic Chemistry

Year: 2007

Issue: 10

Pages: 1653-1658

ISSN (print): 1434-193X

ISSN (electronic): 1099-0690

Publisher: Wiley - VCH Verlag GmbH & Co. KGaA

URL: http://dx.doi.org/10.1002/ejoc.200601099

DOI: 10.1002/ejoc.200601099


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