Synthesis and two-photon absorption of highly soluble three-branched fluorenylene-vinylene derivatives

Two new three-branched fluorenylene-vinylene derivatives were synthesized by triple Heck-type or Horner–Wadsworth–Emmons reactions. Their one-photon absorption and fluorescence as well as their two-photon absorption properties are reported. These compounds, which combine very high solubility in orga...

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Bibliographic Details
Published inTetrahedron letters Vol. 44; no. 44; pp. 8121 - 8125
Main Authors Mongin, Olivier, Porrès, Laurent, Katan, Claudine, Pons, Thomas, Mertz, Jerome, Blanchard-Desce, Mireille
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 27.10.2003
Elsevier
Subjects
Chemical Sciences
Chemistry
Chemistry, Organic
fluorene
Heck coupling
Horner–Wadsworth–Emmons reaction
nonlinear optics (NLO)
or physical chemistry
Physical Sciences
Science & Technology
Theoretical and
two-photon absorption (TPA)
two-photon-excited fluorescence (TPEF)
nonlinear optics (NLO)
Horner–Wadsworth–Emmons reaction
two-photon-excited fluorescence (TPEF)
fluorene
Heck coupling
two-photon absorption (TPA)
STORAGE
DESIGN
FLUOROPHORES
DYES
COOPERATIVE ENHANCEMENT
SALTS
MOLECULES
Horner-Wadsworth-Emmons reaction
NONLINEAR-OPTICAL PROPERTIES
CHROMOPHORES
EXCITATION CROSS-SECTIONS
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Summary:Two new three-branched fluorenylene-vinylene derivatives were synthesized by triple Heck-type or Horner–Wadsworth–Emmons reactions. Their one-photon absorption and fluorescence as well as their two-photon absorption properties are reported. These compounds, which combine very high solubility in organic solvents, high fluorescence quantum yield and giant two-photon absorption cross-sections in the red-NIR region (up to 3660 GM, in the femtosecond regime) are promising candidates for both optical power limiting applications and two-photon laser scanning microscopy. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2003.09.025