Diaroyl(methanato)boron difluoride compounds as medium-sensitive two-photon fluorescent probes

被引:180
作者
Cogné-Laage, E
Allemand, JF
Ruel, O
Baudin, JB
Croquette, V
Blanchard-Desce, M
Jullien, L
机构
[1] Ecole Normale Super, CNRS, UMR 8640, Dept Chim, F-75231 Paris 05, France
[2] Ecole Normale Super, CNRS, UMR 8550, Dept Phys, F-75231 Paris, France
[3] Univ Rennes 1, Inst Chim, CNRS, UMR 6510, F-35042 Rennes, France
关键词
boron; fluorescent probes; structure-activity relationships; two-photon absorption;
D O I
10.1002/chem.200305321
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This paper evaluates the use of diaroyl(methanato)boron difluoride compounds for designing efficient fluorescent probes through two-photon absorption. Three different pathways allowing for the syntheses of symmetrical and dissymmetrical molecules are reported. The stable diaroyl(methanato)boron difluoride derivatives can be easily obtained in good yields. They exhibit a large one-photon absorption that is easily tuned in the near-UV range. Their strong fluorescence emission covers the whole visible domain. In addition to these attractive linear properties, several diaroyl(methanato)boron difluoride derivatives possess significant cross sections for two-photon absorption. The derived structure-property relationships are promising for designing new generations of molecules relying on the diaroyl(methanato)boron difluoride backbone.
引用
收藏
页码:1445 / 1455
页数:11
相关论文
共 93 条
  • [51] Mechanisms for enhancement of two-photon absorption in donor-acceptor conjugated chromophores
    Kogej, T
    Beljonne, D
    Meyers, F
    Perry, JW
    Marder, SR
    Brédas, JL
    [J]. CHEMICAL PHYSICS LETTERS, 1998, 298 (1-3) : 1 - 6
  • [52] KRAPCHO AP, 1973, TETRAHEDRON LETT, P957
  • [53] SOME 3-CYANO-4,6-DIARYL-2-PYRIDONES WITH LUMINESCENT PROPERTIES
    KUTHAN, J
    NESVADBA, P
    POPL, M
    FAHNRICH, J
    [J]. COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1979, 44 (08) : 2409 - 2416
  • [54] Two-photon absorption and second hyperpolarizability of the linear quadrupolar molecule
    Lee, WH
    Cho, MH
    Jeon, SJ
    Cho, BR
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2000, 104 (47) : 11033 - 11040
  • [55] Two-photon absorption and nonlinear optical properties of octupolar molecules
    Lee, WH
    Lee, H
    Kim, JA
    Choi, JH
    Cho, MH
    Jeon, SJ
    Cho, BR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (43) : 10658 - 10667
  • [56] Electronic and vibronic contributions to two-photon absorption of molecules with multi-branched structures
    Macak, P
    Luo, Y
    Norman, P
    Ågren, H
    [J]. JOURNAL OF CHEMICAL PHYSICS, 2000, 113 (17) : 7055 - 7061
  • [57] LARGE 1ST HYPERPOLARIZABILITIES IN PUSH-PULL POLYENES BY TUNING OF THE BOND-LENGTH ALTERNATION AND AROMATICITY
    MARDER, SR
    CHENG, LT
    TIEMANN, BG
    FRIEDLI, AC
    BLANCHARDDESCE, M
    PERRY, JW
    SKINDHOJ, J
    [J]. SCIENCE, 1994, 263 (5146) : 511 - 514
  • [58] A dozen years of single-molecule spectroscopy in physics, chemistry, and biophysics
    Moerner, WE
    [J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2002, 106 (05) : 910 - 927
  • [59] Synthesis and photophysical properties of new conjugated fluorophores designed for two-photon-excited fluorescence
    Mongin, O
    Porrès, L
    Moreaux, L
    Mertz, J
    Blanchard-Desce, M
    [J]. ORGANIC LETTERS, 2002, 4 (05) : 719 - 722
  • [60] Two-photon absorption and optical power limiting of bifluorene molecule
    Morel, Y
    Irimia, A
    Najechalski, P
    Kervella, Y
    Stephan, O
    Baldeck, PL
    Andraud, C
    [J]. JOURNAL OF CHEMICAL PHYSICS, 2001, 114 (12) : 5391 - 5396