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A Closely-Coupled Pyrene Dimer Having Unusually Intense Fluorescence

Lookup NU author(s): Professor Andrew Benniston, Emeritus Professor Anthony Harriman, Donald Lawrie, Sarah Rostron


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A synthetic route is described for the preparation of 1,4-di(1-pyrenyl) butadiyne. The target compound, after purification by extensive column chromatography, has been characterized by NMR and exact-mass spectrometry. This material is highly-fluorescent in solution and, relative to pyrene, strongly absorbing in the near-UV region. Phosphorescence is observed at 77 K and formation of the metastable triplet state has been confirmed by laser flash photolysis. In marked contrast to pyrene, fluorescence from the target compound is not susceptible to self-quenching nor to the presence of dissolved oxygen. The average conformation of the molecule has been established by molecular modeling. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Publication metadata

Author(s): Benniston AC, Harriman A, Lawrie DJ, Rostron SA

Publication type: Article

Publication status: Published

Journal: European Journal of Organic Chemistry

Year: 2004

Volume: 2004

Issue: 10

Pages: 2272-2276

Print publication date: 05/05/2004

ISSN (print): 1434-193X

ISSN (electronic): 1099-0690

Publisher: Wiley-VCH Verlag GmbH & Co KGaA


DOI: 10.1002/ejoc.200400028


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