Progress in the enhancement of electro-optic coefficients and orientation stability for organic second-order nonlinear optical materials

Liu, Jialei; Ouyang, Canbin; Huo, Fuyang; He, Wei; Cao, Aocheng

doi:10.1016/j.dyepig.2020.108509

Cited by 121 publications

(86 citation statements)

References 189 publications

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“…The development of high‐performance organic materials with extensive applications has become an important field of research . Recently, the interest on subphthalocyanine (SubPc) and their derivatives has been enlarged because of their multiple technological applications which include organic optoelectronics.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Optoelectronic Property of Axial‐Substituted Subphthalocyanines

Wang

Zhang

et al. 2020

ChemistryOpen

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Two novel substituted subphthalocyanines have been prepared introducing m‐hydroxybenzoic acid and m‐hydroxyphenylacetic acid into the axial position of bromo‐subphthalocyanine. The compounds have been characterized by Fourier transform infrared (FT‐IR), Nuclear Magnetic Resonance (NMR) and single‐crystal X‐rays diffraction (XRD) methods. Their photophysical properties show that the axial substitution results into a relatively higher fluorescence quantum efficiency (ΦF=5.74 for m‐hydroxybenzoic acid and 9.09 % for m‐hydroxyphenylacetic acid) in comparison with that of the prototype compound, despite the almost negligible influence on the maximum absorption or the emission position. Moreover, the electrochemical behaviors show that the axial‐substituted subphthalocyanines also exhibit enhanced specific capacitances of 395 F/g (m‐hydroxybenzoic acid) and 362 F/g (m‐hydroxyphenylacetic acid) compared with 342 F/g (the prototype) to the largest capacitance at the scan rate of 5 mV/s, and the significantly larger capacitance retentions of 83.6 % and 82.1 % versus 37.3 % upon density up to 3 A/g. These results show the potential of these axial‐substituted subphthalocyanines in the use as organic photovoltaics and supercapacitors.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Optoelectronic Property of Axial‐Substituted Subphthalocyanines

Wang

Zhang

et al. 2020

ChemistryOpen

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“…In recent years, organic NLO (nonlinear optical) materials have attained great interest due to their remarkable uses in photonics and optoelectronics comprising optical signal processing, optical communications, optical data storage and optoelectronic transfer [ 19 , 20 , 21 ]. To display prominent second-order NLO properties, a molecule should be non-centrosymmetric along with intramolecular charge transfer transitions, a large transition dipole moment and a huge difference in the molecular dipole moment at the ground and excited state [ 20 , 22 ]. It can be attained in linear organic compounds by substituting electron-donating and withdrawing groups as it happens in conventional organic dipolar push–pull systems [ 23 ].…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of 5-Aryl-N-(pyrazin-2-yl)thiophene-2-carboxamides via Suzuki Cross-Coupling Reactions, Their Electronic and Nonlinear Optical Properties through DFT Calculations

et al. 2021

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Synthesis of 5-aryl-N-(pyrazin-2-yl)thiophene-2-carboxamides (4a–4n) by a Suzuki cross-coupling reaction of 5-bromo-N-(pyrazin-2-yl)thiophene-2-carboxamide (3) with various aryl/heteroaryl boronic acids/pinacol esters was observed in this article. The intermediate compound 3 was prepared by condensation of pyrazin-2-amine (1) with 5-bromothiophene-2-carboxylic acid (2) mediated by TiCl4. The target pyrazine analogs (4a–4n) were confirmed by NMR and mass spectrometry. In DFT calculation of target molecules, several reactivity parameters like FMOs (EHOMO, ELUMO), HOMO–LUMO energy gap, electron affinity (A), ionization energy (I), electrophilicity index (ω), chemical softness (σ) and chemical hardness (η) were considered and discussed. Effect of various substituents was observed on values of the HOMO–LUMO energy gap and hyperpolarizability. The p-electronic delocalization extended over pyrazine, benzene and thiophene was examined in studying the NLO behavior. The chemical shifts of 1H NMR of all the synthesized compounds 4a–4n were calculated and compared with the experimental values.

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“…During three recent decades much efforts have been spent for obtaining effective push‐pull organic chromophores providing high molecular nonlinear‐optical (NLO) response to the applied intense electric field. Such chromophores consist of a donor (D) and an acceptor (A) moieties linked by a π‐conjugated bridge, and they serve molecular source of the effect when introduced in the polymer matrix in search for new materials with NLO activity [1–7] . In such D‐π‐A arrangement, efficient intramolecular charge transfer (ICT) from donor to acceptor should take place, resulting in a significant chromophore polarization resulting in the enhanced first hyperpolarizability – molecular quadratic NLO characteristic.…”

Section: Introductionmentioning

confidence: 99%

“…Dialkylarylamine donors seem to be most popular components of NLO chromophores, [27–33] the possibility to vary substituents both in alkyl and aromatic parts,thus tuning high hyperpolarizability of chromophores incorporated into an electrooptic (EO) material, is among their attractive features [1–15,20] …”

Section: Introductionmentioning

confidence: 99%

Composing NLO Chromophore as a Puzzle: Electrochemistry‐based Approach to Design and Effectiveness

et al. 2021

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A series of D‐π‐A, D‐π‐D′‐π‐A, D‐π‐A′‐π‐A nonlinear optical chromophores with vinylene π‐electron bridges or bridges with π‐deficient/π‐excessive heterocyclic moieties along with the corresponding precursors D‐vinylene, D‐π‐D′, D′‐π‐A, D‐π‐A′ and A′‐π‐A are synthesized and studied both experimentally and computationally. The effect of the heterocycle in the π‐electron bridge on the oxidation/reduction potentials and the energy gap (ΔEel) is investigated in detail. The properties of the D‐π‐A′(D′)‐π‐A chromophores are shown to correlate with those of building blocks: the oxidation potential is determined by the D‐vinylene, and the reduction potential is determined by A′(D′)‐π‐A truncated compounds. The contribution of the acceptor to the oxidation potential of chromophores in comparison with those of the precursors was estimated and analyzed in terms of electronic communication between the end groups. A good correlation between the ΔEel and the chromophores’ first hyperpolarizability is revealed.

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Progress in the enhancement of electro-optic coefficients and orientation stability for organic second-order nonlinear optical materials

Cited by 121 publications

References 189 publications

Synthesis, Characterization and Optoelectronic Property of Axial‐Substituted Subphthalocyanines

Synthesis, Characterization and Optoelectronic Property of Axial‐Substituted Subphthalocyanines

Facile Synthesis of 5-Aryl-N-(pyrazin-2-yl)thiophene-2-carboxamides via Suzuki Cross-Coupling Reactions, Their Electronic and Nonlinear Optical Properties through DFT Calculations

Composing NLO Chromophore as a Puzzle: Electrochemistry‐based Approach to Design and Effectiveness

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