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

被引:182
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 [J].
Kogej, T ;
Beljonne, D ;
Meyers, F ;
Perry, JW ;
Marder, SR ;
Brédas, JL .
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 [J].
KUTHAN, J ;
NESVADBA, P ;
POPL, M ;
FAHNRICH, J .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1979, 44 (08) :2409-2416
[54]   Two-photon absorption and second hyperpolarizability of the linear quadrupolar molecule [J].
Lee, WH ;
Cho, MH ;
Jeon, SJ ;
Cho, BR .
JOURNAL OF PHYSICAL CHEMISTRY A, 2000, 104 (47) :11033-11040
[55]   Two-photon absorption and nonlinear optical properties of octupolar molecules [J].
Lee, WH ;
Lee, H ;
Kim, JA ;
Choi, JH ;
Cho, MH ;
Jeon, SJ ;
Cho, BR .
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 [J].
Macak, P ;
Luo, Y ;
Norman, P ;
Ågren, H .
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 [J].
MARDER, SR ;
CHENG, LT ;
TIEMANN, BG ;
FRIEDLI, AC ;
BLANCHARDDESCE, M ;
PERRY, JW ;
SKINDHOJ, J .
SCIENCE, 1994, 263 (5146) :511-514
[58]   A dozen years of single-molecule spectroscopy in physics, chemistry, and biophysics [J].
Moerner, WE .
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 [J].
Mongin, O ;
Porrès, L ;
Moreaux, L ;
Mertz, J ;
Blanchard-Desce, M .
ORGANIC LETTERS, 2002, 4 (05) :719-722
[60]   Two-photon absorption and optical power limiting of bifluorene molecule [J].
Morel, Y ;
Irimia, A ;
Najechalski, P ;
Kervella, Y ;
Stephan, O ;
Baldeck, PL ;
Andraud, C .
JOURNAL OF CHEMICAL PHYSICS, 2001, 114 (12) :5391-5396