Synthesis and Spectral Tuning of Novel Triphenylamine‐Based Derivatives Containing Electron Donor‐Acceptor Groups

Gao, Fang; Liu, Jian; Yang, Long; Wang, Qi; Li, Hongru; Zhang, Shengtao

doi:10.1002/cjoc.201090177

Cited by 6 publications

(1 citation statement)

References 44 publications

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“…In turn, this leads to the death of the cation radical without the emission of light. To solve this issue, efforts have been made to incorporate TPA moieties into the polymer backbone or in the side chain of the polymer, and some important results have been obtained . Similarly, the stability of the radical cation mainly depends on the substitution and the orientation of the substitution on TPA.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent, electroactive, thermally stable triphenylamine‐ and naphthalene‐based polyimides for optoelectronic applications

Khalid

Akhter²,

Siddiqi

2016

J of Applied Polymer Sci

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To tune the photophysical properties of polyimides (PIs), a diamine containing naphthalene and triphenylamine units, N 1 -(4-aminophenyl)-N 1 -[(4-naphthalene-2-yloxy)phenyl]benzene-1,4-diamine (DA), was synthesized. A series of fluorescent electroactive new PIs from synthesized DA were prepared with conventional thermal imidization with dianhydride. The selected dianhydride were used to study and compare the effects of rigid planar phenyl, flexible phenoxy, and nonplanar flexible hexafluoroisopropyidene and carbonyl groups in the main polymer backbone on the optoelectronic properties and processability of materials. The structures of the synthesized diamine and its PIs were evaluated by spectral and CHNS elemental analysis. The optoelectronic and thermal properties of PIs revealed intense blue-light emission (428-477 nm), a low oxidation potential (0.3-1.3 V), and a lower highest occupied molecular orbital-lowest unoccupied molecular orbital gap (2.92-3.21 eV). The observed behavior and properties of our synthesized PIs suggest their potential as future hole-transport materials in optoelectronic applications. V C 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 44526.

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Section: Introductionmentioning

confidence: 99%

Fluorescent, electroactive, thermally stable triphenylamine‐ and naphthalene‐based polyimides for optoelectronic applications

Khalid

Akhter²,

Siddiqi

2016

J of Applied Polymer Sci

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Two-Photon Optical Properties of Novel Branched Conjugated Derivatives Carrying Benzophenone Moiety with Various Electron Donor-Acceptor Substituent Groups

Yang

Liu

et al. 2010

J Fluoresc

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This paper presents a range of novel new branched conjugated dyes containing benzophenone moiety. As compared with those of 4-(p-benzoyl-styrene)yl-4'-(styrene)yl-triphenylamine (C1) and 4-(p-benzoyl-styrene)yl-4'-3,4,5-trimethoxyl-styrene)yl-triphenylamine (C2), the maximal linear absorption and emission wavelength of 4-(p-benzoyl-styrene)yl-4'-(p'-nitro-styrene)yl-triphenylamine (C3) displays red-shifted remarkably, While the fluorescence quantum yields of C3 are lower than those of C1 and C2 in various solvents. The fluorescence lifetimes of the derivatives were measured, and radiative and non-radiative transition constants of the derivatives were calculated. Two-photon absorption (TPA) optical data of the derivatives were measured by Ti:sapphire femtosecond laser tuning from 720 to 880 nm at intervals of 20 nm. TPA induced fluorescence emission of C3 is red-shifted with respected to that of C1 and C2. TPA cross sections of C3 are larger than those of C1 and C2 in various excited laser frequencies. TPA cross section of C2 and C3 are much larger than those of 3,4,5-(trimethoxylstyrene)yl-triphenylamine (C4) and 4-(p-nitrostyrene)yl-triphenylamine (C5) respectively under various near-IR Ti:sapphire femtosecond laser wavelength. C1 and C2 show similar one- and two- photon optical nature. Geometry optimization with ab initio method confirms that C3 has different electron density distribution, the energy levels in frontier orbitals, the dipole moment changes, the absorption and emission spectroscopy from those of C1 and C2. The cyclic voltammograms of the derivatives were detected in methylene chloride at various scan rates, and the energy of frontier orbials were estimated further from the redox potentials.

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Triphenylamine-Based Fluorescent Styryl Dyes: DFT, TD-DFT and Non-Linear Optical Property Study

et al. 2017

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The electronic structures and spectroscopic properties of triphenylamine-based monostyryl and bis(styryl) dyes were studied using quantum chemical methods. The ground-state geometries of these dyes were optimized using the density functional theory (DFT) method. The lowest singlet excited state was optimized using time-dependent density functional theory (TD-DFT). The absorption was also calculated using the ground-state geometries. All the calculations were carried out in the gas phase and in solvent. The results indicate that the absorption maxima calculated using the TD-DFT are in good agreement with those obtained experimentally. These dyes possess a large second-order non-linear property and this is mainly due to the strong donor-π-acceptor conjugation which is attributed to the excited state intramolecular charge transfer (ICT). There is a relationship between the hardness and first hyperpolarizability and second hyperpolarizability of mono- and bis(styryl) dyes. The efficiency of the intersystem crossing process can be improved by reducing the energy gap between the singlet and triplet excited states.

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Synthesis and Spectral Tuning of Novel Triphenylamine‐Based Derivatives Containing Electron Donor‐Acceptor Groups

Cited by 6 publications

References 44 publications

Fluorescent, electroactive, thermally stable triphenylamine‐ and naphthalene‐based polyimides for optoelectronic applications

Fluorescent, electroactive, thermally stable triphenylamine‐ and naphthalene‐based polyimides for optoelectronic applications

Two-Photon Optical Properties of Novel Branched Conjugated Derivatives Carrying Benzophenone Moiety with Various Electron Donor-Acceptor Substituent Groups

Triphenylamine-Based Fluorescent Styryl Dyes: DFT, TD-DFT and Non-Linear Optical Property Study

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