Synthesis and electro-optic properties of novel Y-type polyester containing nitrothiazolylazoresorcinoxy group with highly enhanced thermal stability of dipole alignment

Choe, Kang Yun; Kim, Jung-Eun; Lee, Ju‐Yeon

doi:10.1016/j.dyepig.2016.06.040

Cited by 4 publications

(1 citation statement)

References 48 publications

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“…At the same time, large optical nonlinearities are accompanied by temporal responses that can be as low as in the femtosecond range [3], raising hopes for applications in optical signal processing, e.g., in all-optical switching [4][5][6]. On the synthetic side, a considerable body of information has been accumulated about how to maximize NLO response of organic compounds and led to the determination of molecular design principles for organic [7][8][9][10] and organometallic NLO chromophores [11][12][13][14]. These principles are now commonplace tools that assist the design of new small-molecular and polymeric compounds for nonlinear optics.…”

Section: Introductionmentioning

confidence: 99%

Nonlinear Optical Pigments. Two-Photon Absorption in Crosslinked Conjugated Polymers and Prospects for Remote Nonlinear Optical Thermometry

2020

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Nonlinear optical (NLO) pigments are compounds insoluble in solvents that exhibit phenomena related to nonlinear optical susceptibilities (χ(n) where n = 2,3,...), e.g., two-photon absorption (2PA) which is related to the imaginary part of χ(3). Determination of spectrally-resolved 2PA properties for NLO pigments of macromolecular nature, such as coordination polymers or crosslinked polymers, has long been a challenging issue due to their particulate form, precluding characterizations with standard techniques such as Z-scan. In this contribution, we investigate thus far unknown spectrally-resolved 2PA properties of a new subclass of NLO pigments—crosslinked conjugated polymers. The studied compounds are built up from electron-donating (triphenylamine) and electron-withdrawing (2,2’-bipyridine) structural fragments joined by vinylene (Pol1) or vinyl(4-ethynylphenyl) (Pol2) aromatic bridges. 2PA properties of these polymers have been characterized in broad spectral range by specially modified two-photon excited fluorescence (TPEF) techniques: solid state TPEF (SSTPEF) and internal standard TPEF (ISTPEF). The impact of self-aggregation of aromatic backbones on the 2PA properties of the polymers has been evaluated through extended comparisons of NLO parameters, i.e., 2PA cross sections (σ2) and molar-mass normalized 2PA merit factors (σ2/M) with those of small-molecular model compounds: Mod1 and Mod2. By doing this, we found that the 2PA response of Pol1 and Pol2 is improved 2–3 times versus respective model compounds in the solid state form. Further comparisons with 2PA results collected for diluted solutions of Mod1 and Mod2 supports the notion that self-aggregated structure contributes to the observed enhancement of 2PA response. On the other hand, it is clear that Pol1 and Pol2 suffer from aggregation-caused quenching phenomenon, well reflected in time-resolved fluorescence properties as well as in relatively low values of quantum yield of fluorescence. Accordingly, despite improved intrinsic 2PA response, the effective intensity of two-photon excited emission for Pol1 and Pol2 is slightly lower relative to Mod1 and Mod2. Finally, we explore temperature-resolved luminescence properties under one- (377 nm), two- (820 nm), and three-photon excitation (1020 nm) conditions of postsynthetically Eu3+-functionalized material, Pol1-Eu, and discuss its suitability for temperature sensing applications.

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Section: Introductionmentioning

confidence: 99%

Nonlinear Optical Pigments. Two-Photon Absorption in Crosslinked Conjugated Polymers and Prospects for Remote Nonlinear Optical Thermometry

2020

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The role of the Terminal Benzene Derivatives in Triphenylamine‐Based Oxime Esters for Free Radical Photopolymerization

Hsieh,

Chen

2024

ChemPhotoChem

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In this study, we investigate the effect of terminal benzene derivatives in triphenylamine‐based oxime esters on their photoreactivity. Five novel oxime esters ( Miko series) that containing different benzene derivatives as terminal groups, were synthesized. The electronic properties of the substituents on the benzene ring range from electron‐donating to electron‐withdrawing. Specifically, a methoxy benzene for Miko‐MOB, tert‐butyl benezene for Miko‐t‐Bu, chloro benzene for Miko‐CB, trifluoromethyl benzene for Miko‐TFM, and nitro benzene for Miko‐NB. Additionally, a compound with benzene only as the terminal substituent (TP‐1) was selected for comparision. All the new compounds exhibited higher molar extinction coefficients than TP‐1. Additionally, the steady‐state photolysis and electron spin resonance (ESR) properties would decrease from the electron‐donating substitutes to electron‐withdrawing substitutes. Finally, these oxime esters are utilized in Type I photoinitiating systems for the free radical polymerization of trimethylolpropane triacrylate (TMPTA) under UV or LED@405 nm light irradiation conditions. Among all formulations, Miko‐MOB demonstrated the highest double bond conversion efficiency under both UV and LED@405 nm light irradiation. Thus, terminal benzene derivatives in oxime esters play an important role in tuning the optical and photochemical reaction performance, offering significant value for the design strategy of such photoinitiators.

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High stability poly(N-adamantyl-exo-norbornene-5,6-dicarboximide) and phenyl vinylene thiophene electro-optic host-guest system

Spring

Qiu

Yokoyama

2016

European Polymer Journal

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Synthesis and electro-optic properties of novel Y-type polyester containing nitrothiazolylazoresorcinoxy group with highly enhanced thermal stability of dipole alignment

Cited by 4 publications

References 48 publications

Nonlinear Optical Pigments. Two-Photon Absorption in Crosslinked Conjugated Polymers and Prospects for Remote Nonlinear Optical Thermometry

Nonlinear Optical Pigments. Two-Photon Absorption in Crosslinked Conjugated Polymers and Prospects for Remote Nonlinear Optical Thermometry

The role of the Terminal Benzene Derivatives in Triphenylamine‐Based Oxime Esters for Free Radical Photopolymerization

High stability poly(N-adamantyl-exo-norbornene-5,6-dicarboximide) and phenyl vinylene thiophene electro-optic host-guest system

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