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Intramolecular energy transfer in pyrene-bodipy molecular dyads and triads

Lookup NU author(s): Emeritus Professor Anthony Harriman, James Rostron


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Molecules bearing a 4,4-difluoro-8-(aryl)-1,3,5,7-tetramethyl-2,6-diethyl- 4-bora-3a,4a-diaza-s-indacene (bodipy) core and 1-pyrenyl-1-phenyl-4-(1- ethynylpyrene), or 1-phenyl-4-[1-ethynyl-(6-ethynylpyrene)pyrene] units were constructed in a step-by-step procedure based on palladium(0)-promoted cross-coupling reactions with the required preconstructed modules. X-ray structures of single crystals reveal a twisted arrangement of the two chromophores. In one case, an almost perfect orthogonal arrangement is found. These dyes are strongly luminescent in solution and display rich electrochemistry in which all redox processes of the bodipy and pyrene fragments are clearly resolved. The absorption spectra indicate that the bodipy and pyrene chromophores are spectrally isolated, thereby inducing a large "virtual" Stokes shift. The latter is realised by efficient transfer of intramolecular excitation energy by the Förster dipole-dipole mechanism. The rate of energy transfer depends on the structure of the dualdye system and decreases as the centre-to-centre separation increases. The energy transfer efficiency, however, exceeds 90% in all cases. The linkage of two pyrene residues by an ethyne group leads to a decrease in the energy-transfer efficiency, with the two polycycles acting as a single chromophore. The directly linked bodipypyrene dual dye binds to DNA and operates as an efficient solar concentrator when dispersed in plastic. © 2005 Wiley-VCH Verlag GmbH & Co. KgaA.

Publication metadata

Author(s): Ziessel R, Goze C, Ulrich G, Cesario M, Retailleau P, Harriman A, Rostron JP

Publication type: Article

Publication status: Published

Journal: Chemistry: A European Journal

Year: 2005

Volume: 11

Issue: 24

Pages: 7366-7378

Print publication date: 09/12/2005

ISSN (print): 0947-6539

ISSN (electronic): 1521-3765

Publisher: Wiley - VCH Verlag GmbH & Co. KGaA


DOI: 10.1002/chem.200500373


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