α-Hydroxy Ketone Precursors Leading to a Novel Class of Electro-optic Acceptors

He, Mingqian; Leslie, Thomas M.; Sinicropi, John A.

doi:10.1021/cm011734t

Cited by 142 publications

(91 citation statements)

References 15 publications

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“…[17] The pentafluorophenyl-and various aryl dendrons were then sequentially introduced to the p-bridge and donor-end of the trienal by carbodiimide-mediated esterification following the procedure described in the literature. [15] Finally, efficient condensation of the dendronized trienal with a strong CF 3 -TCF-type acceptor [19] afforded the desired chromophores TED1-3 in 31-46% overall yields. The entire scheme for the preparation of TED1-3 showed a significantly improved synthetic efficiency in comparison with other EO dendrimers requiring lengthy and tedious synthetic steps.…”

Section: à3mentioning

confidence: 99%

Supramolecular Self‐Assembled Dendritic Nonlinear Optical Chromophores: Fine‐Tuning of Arene–Perfluoroarene Interactions for Ultralarge Electro‐Optic Activity and Enhanced Thermal Stability

et al. 2009

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Organic second-order nonlinear optical (NLO) materials are being actively pursued due to the increasing potential for application in photonic devices, such as high-speed electro-optic (EO) modulators, optical switches, and frequency converters. [1] For the fabrication of practical EO devices, critical material requirements, such as large EO coefficients, high thermal stability, and low optical loss need to be simultaneously optimized. One of the major problems in optimizing organic EO materials lies in the translation of high molecular nonlinearity into macroscopic EO activity by poling-induced acentric ordering of the dipolar chromophores.[2] Extensive experimental and theoretical studies have shown strong intermolecular electrostatic interaction among high-dipole-moment (m) chromophores to be the major factor defining the EO activity of electric-field-poled organic materials. These studies also suggest that the maximum realizable EO activity could be enhanced by controlling the chromophore shape to prevent stacking. [3] Owning to the unique characteristics of dendrimers (globular and void-containing shape, core encapsulation, structural uniformity, and high end-group functionality), dendritic NLO materials are of particular interest, because they provide opportunities for nanoscale architectural control and molecular and supramolecular engineering to simultaneously improve macroscopic EO activity and thermal stability. Dendritic NLO materials also introduce other auxiliary properties, including optical transparency, chemical and photochemical stability, and compatibility in composite materials.[4] For example, dendritic encapsulation of multiple dendron-modified chromophores [5] and multichromophore dendrimers, [6] as well as the use of dendronized side-chain EO polymers [7] created by post-functionalization, have recently been shown to lead to significantly enhanced EO coefficients in comparison with the conventional chromophore/polymer composites. In order to simultaneously improve their thermal stability and solvent resistance, a novel lattice-hardening approach using a sequential poling and cross-linking process based on the Diels-Alder cycloaddition reaction has been successfully developed to overcome the commonly observed nonlinearity-stability tradeoff in organic EO materials. [8] However, this approach adds a significant complication to both molecule design and the poling process for these highly efficient dendritic EO materials.The arene-perfluoroarene (ArH-ArF) interaction, [9] known as a strong face-to-face interaction between perfluorinated and nonfluorinated aromatic rings, was recently utilized to control supramolecular organization in reversible media including modulating the behavior of liquid-crystalline phases, [10] formation of hydrogels, [11] and templation effects in both solid-state photopolymerization and solution-state organic synthesis.[12] The ArH-ArF interaction was also used to create tightly packed molecular assemblies leading to a new class of supramolecular materials for el...

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Section: à3mentioning

confidence: 99%

Supramolecular Self‐Assembled Dendritic Nonlinear Optical Chromophores: Fine‐Tuning of Arene–Perfluoroarene Interactions for Ultralarge Electro‐Optic Activity and Enhanced Thermal Stability

et al. 2009

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“…The molecular nature of the materials offers considerable design possibilities which should permit to scale up the favourable molecular nonlinear optical properties to macroscopic devices [3][4][5][6][7][8]. Organic nonlinear optical materials with aromatic rings represent a large class of such materials with high nonlinearity, fast response and high optical damage threshold [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Correlation between structural studies and third order NLO properties of selected new quinolinium semi-organic compounds

Bouchouit

Bendeif²,

Ouazzani

et al. 2010

Chemical Physics

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“…10,11,[18][19][20] The precursor polyimide, PI-OH, 4 was also prepared by DOI 10.1007/s13233-011-0410-2 *Corresponding Author. E-mail: dhchoi8803@korea.ac.kr following the method in our previous work.…”

Section: Methodsmentioning

confidence: 99%

“…In order to design a highly active NLO chromophore, tricyanofuran (TCF)-and tricyanopyrroline (TCP)-based chromophores are employed; these are well known to have large permanent dipole moments and to exhibit electronic transitions at a higher wavelength. [8][9][10][11] Although the microscopic nonlinearity of a specific chromophore is relatively high, the macroscopic properties will be governed by the spatial arrangement of the chromophores in the polymer host. At a higher loading concentration, we normally observe a significant reduction in the EO effect due to chromophore aggregation, which is usually driven by strong intermolecular electrostatic interactions.…”

Section: Introductionmentioning

confidence: 99%

Electro-optic effect of a soluble nonlinear optical polyimide containing two different chromophores with different sizes in the side chain

Kim

Hoang²,

Choi³

et al. 2011

Macromol. Res.

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A new soluble and thermally stable nonlinear optical (NLO) polyimide was synthesized by adding both tricyanopyrroline (TCP)-and tricyanofuran (TCF)-based NLO chromophores into the polymer backbone. The NLO polyimide (PI-II) bearing two different chromophores with different sizes has a glass transition temperature of 146 o C and exhibits good film forming properties. The electro-optic coefficient of the film was 84 pm/V at 1.3 µm under a poling field of 80V/µm, even though PI-II has an unusually high chromophore density of approximately 20 wt% of TCP chromophores and 23 wt% of TCF chromophores. Even with a overall chromophore loading of 43 wt%, no severe aggregation effect was observed for the sample that exhibited a relatively high EO coefficient.

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α-Hydroxy Ketone Precursors Leading to a Novel Class of Electro-optic Acceptors

Cited by 142 publications

References 15 publications

Supramolecular Self‐Assembled Dendritic Nonlinear Optical Chromophores: Fine‐Tuning of Arene–Perfluoroarene Interactions for Ultralarge Electro‐Optic Activity and Enhanced Thermal Stability

Supramolecular Self‐Assembled Dendritic Nonlinear Optical Chromophores: Fine‐Tuning of Arene–Perfluoroarene Interactions for Ultralarge Electro‐Optic Activity and Enhanced Thermal Stability

Correlation between structural studies and third order NLO properties of selected new quinolinium semi-organic compounds

Electro-optic effect of a soluble nonlinear optical polyimide containing two different chromophores with different sizes in the side chain

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