Recent progress in second-order nonlinear optical polymers and dendrimers

Cho, Min Ju; Choi, Dong Hoon; Sullivan, Philip A.; Akelaitis, Andrew J. P.; Dalton, Larry R.

doi:10.1016/j.progpolymsci.2008.07.007

Cited by 347 publications

(161 citation statements)

References 242 publications

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“…11 In parallel with the engineering of new NLO dyes for 10 biological multiphoton imaging, there have been rapid advances in the design of molecular NLO materials for telecommunications and photonics applications. 12 Chromophores with large hyperpolarizabilities and high chemical stability are needed for frequency doublers, electro-optic switches and modulators. There 15 is substantial overlap between the molecular design requirements in these two areas.…”

Section: Introductionmentioning

confidence: 99%

Thiophene-based dyes for probing membranes

López‐Duarte

Chairatana

et al. 2015

Org. Biomol. Chem.

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We report the synthesis of four new cationic dipolar push-pull dyes, together with an evaluation of their photophysical and photobiological characteristics pertinent for imaging membranes by fluorescence and second harmonic generation. All four dyes consist of an N,N-diethylaniline electron-donor conjugated to a pyridinium electron-acceptor via a thiophene bridge, with either vinylene (-CH=CH-) or ethynylene 10 (-CC-) linking groups, and with either singly-charged or doubly-charged pyridinium terminals. The absorption and fluorescence behavior of these dyes was compared to a commercially available fluorescent membrane stain, the styryl dye FM4-64. The hyperpolarizabilities of all dyes were compared using hyper-Rayleigh scattering at 800 nm. Cellular uptake, localization, toxicity and phototoxicity were evaluated using tissue cell cultures (HeLa, SK-OV-3 and MDA-231). Replacing the central alkene bridge 15 of FM4-64 with a thiophene does not substantially change the absorption, fluorescence or hyperpolarizability, whereas changing the vinylene-links to ethynylenes shifts the absorption and fluorescence to shorter wavelengths, and reduces the hyperpolarizability by about a factor of two. SHG and fluorescence imaging experiments in live cells showed that the doubly-charged thiophene dyes localize in plasma membranes, and exhibit lower internalization rates compared to FM4-64, resulting in 20 less signal from the cell cytosol. At a typical imaging concentration of 1 µM, the doubly-charged dyes showed no significant light or dark toxicity, whereas the singly-charged dyes are phototoxic even at 0.5 µM, and toxic in the dark at concentrations above 5 µM. The doubly-charged dyes showed phototoxicity at concentrations greater than 10 µM, although they do not generate singlet oxygen, indicating that the phototoxicity is type I rather than type II. Our data demonstrate that the doubly-charged thiophene dyes 25 are more effective than FM4-64 as nonlinear optical imaging agents for live cells.

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Section: Introductionmentioning

confidence: 99%

Thiophene-based dyes for probing membranes

López‐Duarte

Chairatana

et al. 2015

Org. Biomol. Chem.

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“…Significantly, Monguzzi et al have reported energy up-conversion in a multi-component organic polymer at irradiances as low as 10 W m −2 , a level at which the low energy tail of the solar emission spectrum could be captured even without focusing optics [53]. Earlier reports of exceptionally high two-photon absorption cross-sections and enhanced third-order optical nonlinearity [54][55][56] have inspired many other suggestions for exploiting dendrimers in a range of applications extending well-beyond energy harvesting [57][58][59][60][61][62][63][64][65].…”

Section: Multiphoton Processesmentioning

confidence: 99%

Mechanisms of Light Energy Harvesting in Dendrimers and Hyperbranched Polymers

Bradshaw

Andrews

2011

Polymers

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Abstract:Since their earliest synthesis, much interest has arisen in the use of dendritic and structurally allied forms of polymer for light energy harvesting, especially as organic adjuncts for solar energy devices. With the facility to accommodate a proliferation of antenna chromophores, such materials can capture and channel light energy with a high degree of efficiency, each polymer unit potentially delivering the energy of one photon-or more, when optical nonlinearity is involved. To ensure the highest efficiency of operation, it is essential to understand the processes responsible for photon capture and channelling of the resulting electronic excitation. Highlighting the latest theoretical advances, this paper reviews the principal mechanisms, which prove to involve a complex interplay of structural, spectroscopic and electrodynamic properties. Designing materials with the capacity to capture and control light energy facilitates applications that now extend from solar energy to medical photonics.

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“…Is worthy to note that absorption of the hybrid composite at both fundamental and doubled laser frequencies (ω = 1064 nm, and ω 2 = 532 nm, respectively) are not in the resonance regime; this means that the absorption effects in SHG can be neglected and that Eq. (1) can reasonably be applied for the relative evaluation of the (2) S eff χ coefficient of hybrid materials. Figure 6 shows a comparative photoluminiscent spectra of the studied materials recorded from 200 to 900 nm (excitation wavelength was set at λ exc = 373 nm according to the resonance absorption of the hybrid samples).…”

Section: Morphological Afm-analysismentioning

confidence: 99%

“…rodlike dipolar systems. Nevertheless, second-order ONL effects may also arise from some centrosymmetric molecular structures, such as octopolar compounds, which posses a zero overall dipole moment and liquid crystalline (LC) behavior in columnar phases [1][2][3]. The development of octopolar nonlinear optical materials suitable for several applications in optical, nonlinear optical and electro-optical devices is a topic of current interest among many research groups.…”

Section: Introductionmentioning

confidence: 99%

“…The octopolar structures present many other advantages in comparison to the more conventional dipolar molecules. For example, most commonly conjugated dipolar systems, in a supramolecular arrangement, such as a bulk format, can lead to extinction of the macroscopic susceptibility due to anti-parallel alignment of the molecules [2]. In contrast, octopolar molecules, possessing a zero overall dipole moment in both the ground and excited states [6], can ideally be arranged in the bulk phase in a way that their molecular susceptibility is additive [7].…”

Section: Introductionmentioning

confidence: 99%

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Morphology, Linear and Nonlinear Optical Response of Octopolar Chromophores Embedded in a Silica Sonogel Matrix

Torres-Zúñiga

Morales–Saavedra

Hennrich

et al. 2010

Molecular Crystals and Liquid Crystals

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In this work, a liquid crystalline octopolar molecule 1,3,5-tris(ethynylphenyl)benzene- (1) was successfully embedded as dopant chromophore within a SiO 2 based sonogel network in order to prepare stable solid state hybrid materials with intense second harmonic generation (SHG). This recently synthesized octopolar compound exhibit a centrosymmetric C 3 -symmetry structure, which is constituted by an electron-rich core and electron-poor periphery groups. The sonogel method, induced by energetic ultrasonic (US) waves applied at the TEOS/H 2 O reactant mixture interface has proven to be a suitable route in the manufacture of monolithic hybrid systems suitable for optical characterizations. The octopolar-based hybrid samples were comprehensively studied in their morphology, spectroscopic, linear and second-order nonlinear optical (NLO) properties, according to several characterization techniques: epimicroscopy, AFM, UV-Vis-and fluorescence (PL) spectroscopies, and the NLO-SHG-technique. Epimicroscopy, photoluminiscent and absorption spectra evidence an optimal and homogeneous inclusion of the octopolar compounds within the glassy sonogel network. Without necessity of molecular poling processes, the effective quadratic-NLO susceptibility (2) S eff χ of the hybrid was estimated to 13.6x10 -3 pm/V at 1064 nm by SHG-transmission experiments recorded far-off of the resonance regime.

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Recent progress in second-order nonlinear optical polymers and dendrimers

Cited by 347 publications

References 242 publications

Thiophene-based dyes for probing membranes

Thiophene-based dyes for probing membranes

Mechanisms of Light Energy Harvesting in Dendrimers and Hyperbranched Polymers

Morphology, Linear and Nonlinear Optical Response of Octopolar Chromophores Embedded in a Silica Sonogel Matrix

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