A convenient synthesis of push-pull polyenes designed for the elaboration of efficient nonlinear optical materials

Mladenova, M.; Ventelon, Lionel; Blanchard‐Desce, Mireille

doi:10.1016/s0040-4039(99)01443-4

Cited by 23 publications

(6 citation statements)

References 11 publications

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“…All reactions were carried out on a large scale (5Ϫ20 g) with excellent overall yields (b: 84%; c: 81%; e: 88%). These aldehydes were then quantitatively protected as their tetrahydropyranyl (THP) ethers (bЈ, [13] cЈ, eЈ). The noncommercially available aniline 1e was prepared by alkylation of N-butylaniline with 2-(4-Bromobutyl)tetrahydropyran, followed by removal of the THP moiety (see Exp.…”

Section: Synthesismentioning

confidence: 99%

“…1 H NMR (CDCl 3 ): δ ϭ 8.58 (d, J ϭ 5.0 Hz, 2 H, 6-H), 8.44 (s,2 H,H 3 ),7.40 (d,J ϭ 9.0 Hz,4 H,7.36 (d,J ϭ 16.3 Hz,2 H,7.31 (dd,J ϭ 5,J ϭ 1.3 Hz,2 H,6.86 (d,J ϭ 16.3 Hz,2 H,6.62 (d,J ϭ 9.0 Hz,4 H,3.67 (t,J ϭ 6.0 Hz,4 H,3.31 (m,8 H,13,1.81Ϫ1.48 (m,12 H,14,14Ј,1.45Ϫ1.24 (m,4 H,0.94 (t,J ϭ 7.0 Hz,6 H, C 75.87, H 8.49, N 8.43; found C 75.44, H 8.26, N 8.54.…”

Section: 4ј-bis{4-[(butyl)(4-hydroxybutyl)amino]styryl}-22ј-bipyrimentioning

confidence: 99%

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Hydroxy-Functionalized Bipyridine and Tris(bipyridine)metal Chromophores: Synthesis and Optical Properties

et al. 2002

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A new family of symmetrically and unsymmetrically-substituted 4,4Ј-bis[(dialkylamino)styryl]-2,2Ј-bipyridine ligands, containing 1−4 hydroxy groups on their dialkylamino moieties, have been synthesized. They are readily prepared in good to excellent yields from 4,4Ј-dimethyl-2,2Ј-bipyridine and tetrahydropyranyloxy-protected [(hydroxyalkyl)amino]-benzaldehydes. These chromophores display excellent thermal stabilities, with decomposition temperatures of up to 310

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Section: Synthesismentioning

confidence: 99%

Section: 4ј-bis{4-[(butyl)(4-hydroxybutyl)amino]styryl}-22ј-bipyrimentioning

confidence: 99%

Hydroxy-Functionalized Bipyridine and Tris(bipyridine)metal Chromophores: Synthesis and Optical Properties

et al. 2002

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“…Functionalized polyenals can be prepared in quantitative yield from the generic compound by sequential (poly)vinylic homologation. 20 Figure 8. Synthetic route to amphiphilic push-pull polyenic chromophores.…”

Section: Design Of Dipolar Chromophore For Nlo Membrane Imagingmentioning

confidence: 99%

Molecular probes for nonlinear optical imaging of biological membranes

Blanchard‐Desce¹,

Ventelon

Charier

et al. 2001

Linear and Nonlinear Optics of Organic Materials

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Second-harmonic generation (SHG) and two-photon excited fluorescence (TPEF) are nonlinear optical (NLO) phenomena that scale with excitation intensity squared, and hence give rise to an intrinsic 3-dimensional resolution when used in microscopic imaging. TPEF microscopy has gained widespread popularity in the biology community whereas SHG microscopy promises to be a powerful tool because of its sensitivity to local asymmetry. We have implemented an approach toward the design of NLO-probes specifically adapted for SHG and/or TPEF imaging of biological membranes. Our strategy is based on the design of nanoscale amphiphilic NLO-phores. We have prepared symmetrical bolaamphiphilic fluorophores combining very high two-photon absorption (TPA) cross-sections in the visible red region and affinity for cellular membranes. Their incorporation and orientation in lipid membranes can be monitored via TPEF anisotropy. We have also prepared amphiphilic push-pull chromophores exhibiting both large TPA cross-sections and very large first hyperpolarizabilities in the near-IR region. These NLO-probes have proved to be particularly useful for imaging of biological membranes by simultaneous SHG and TPEF microscopy and offer attractive prospects for real-time imaging of fundamental biological processes such as adhesion, fusion or reporting of membrane potentials.

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“…Highly conjugated π-electron compounds such as aryl-substituted dienes and polyenes have gained a lot of attention because of the wide range of their applications in functional materials such as organic fluorescent probes, electroluminescent devices, and nonlinear optical materials [ 1 , 2 , 3 , 4 , 5 ].…”

Section: Introductionmentioning

confidence: 99%

1-(Triethoxysilyl)buta-1,3-dienes—New Building Blocks for Stereoselective Synthesis of Unsymmetrical (E,E)-1,4-Disubstituted 1,3-dienes

2015

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A convenient synthesis of push-pull polyenes designed for the elaboration of efficient nonlinear optical materials

Cited by 23 publications

References 11 publications

Hydroxy-Functionalized Bipyridine and Tris(bipyridine)metal Chromophores: Synthesis and Optical Properties

Hydroxy-Functionalized Bipyridine and Tris(bipyridine)metal Chromophores: Synthesis and Optical Properties

Molecular probes for nonlinear optical imaging of biological membranes

1-(Triethoxysilyl)buta-1,3-dienes—New Building Blocks for Stereoselective Synthesis of Unsymmetrical (E,E)-1,4-Disubstituted 1,3-dienes

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