A closely-coupled pyrene dimer having unusually intense fluorescence

被引:37
作者
Benniston, AC [1 ]
Harriman, A [1 ]
Lawrie, DJ [1 ]
Rostron, SA [1 ]
机构
[1] Newcastle Univ, Sch Nat Sci Chem, Mol Photon Lab, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England
关键词
fluorescence; sensors; pyrene; charge transfer; glaser coupling;
D O I
10.1002/ejoc.200400028
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
引用
收藏
页码:2272 / 2276
页数:5
相关论文
共 33 条
  • [1] CHARGE RECOMBINATION PROCESS OF ION-PAIR STATE PRODUCED BY EXCITATION OF CHARGE-TRANSFER COMPLEX IN ACETONITRILE SOLUTION - ESSENTIALLY DIFFERENT CHARACTER OF ITS ENERGY-GAP DEPENDENCE FROM THAT OF GEMINATE ION-PAIR FORMED BY ENCOUNTER BETWEEN FLUORESCER AND QUENCHER
    ASAHI, T
    MATAGA, N
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1989, 93 (18) : 6575 - 6578
  • [2] The photophysical properties of a pyrene-thiophene-terpyridine conjugate and of its zinc(II) and ruthenium(II) complexes
    Benniston, AC
    Harriman, A
    Lawrie, DJ
    Mayeux, A
    [J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2004, 6 (01) : 51 - 57
  • [3] Bu''nau G. v., 1970, RANG DALESPHARMACOLO, V74, P1294, DOI [10.1002/bbpc.19700741223, DOI 10.1002/BBPC.19700741223]
  • [4] DIRECT AND SENSITIZED PHOTOOXIDATION OF CYANINE DYES
    BYERS, GW
    GROSS, S
    HENRICHS, PM
    [J]. PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1976, 23 (01) : 37 - 43
  • [5] Pyrene covalently anchored on a large external surface area zeolite as a selective heterogeneous sensor for iodide
    Corma, A
    Galletero, MS
    García, H
    Palomares, E
    Rey, F
    [J]. CHEMICAL COMMUNICATIONS, 2002, (10) : 1100 - 1101
  • [6] Design, synthesis, and evaluation of bile acid-based molecular tweezers
    DSouza, LJ
    Maitra, U
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) : 9494 - 9502
  • [7] Dynamics for the assembly of pyrene-γ-cyclodextrin host-guest complexes
    Dyck, ASM
    Kisiel, U
    Bohne, C
    [J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2003, 107 (42) : 11652 - 11659
  • [8] ENERGY GAP LAW FOR RADIATIONLESS TRANSITIONS IN LARGE MOLECULES
    ENGLMAN, R
    JORTNER, J
    [J]. MOLECULAR PHYSICS, 1970, 18 (02) : 145 - +
  • [9] Optical oxygen sensor based on fluorescence change of pyrene-1-butyric acid chemisorption film on an anodic oxidation aluminium plate
    Fujiwara, Y
    Okura, I
    Miyashita, T
    Amao, Y
    [J]. ANALYTICA CHIMICA ACTA, 2002, 471 (01) : 25 - 32
  • [10] Photophysical properties of pyrene-(2,2 '-bipyridine) dyads
    Harriman, A
    Hissler, M
    Ziessel, R
    [J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 1999, 1 (18) : 4203 - 4211