Triphenylamine isophorone derivatives with two photon absorption: Photo-physical property, DFT study and bio-imaging

Gan, Xiaoping; Wang, Yang; Ge, Xinping; Li, Wei; Zhang, Xiuzhen; Zhu, Weiju; Wu, Jieying; Tian, Yupeng

doi:10.1016/j.dyepig.2015.04.007

Cited by 43 publications

(16 citation statements)

References 43 publications

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“…[15][16][17] ICT plays indeed as ignificant role in determining the non-linear properties of such push-pull systemsa nd significant tuning of the non-linear responses can be achieved by tuning the ICT. [21,22] Interestingly,al arger 2PAr esponse was recently observed in quadrupolar D-p-A-p-D structuresw here two diphenylamines replacedt he analogous dimethylamino lateral groups. [19,20] In particular,t he triphenylamine donor was extensively used in optical materials due to its high electron donating capability ande ffective conjugation length.…”

Section: Introductionmentioning

confidence: 86%

“…[19,20] In particular,t he triphenylamine donor was extensively used in optical materials due to its high electron donating capability ande ffective conjugation length. [21,22] Interestingly,al arger 2PAr esponse was recently observed in quadrupolar D-p-A-p-D structuresw here two diphenylamines replacedt he analogous dimethylamino lateral groups. [23] Moreover,t he use of chargedDa nd Ag roups could be an effectives trategy to increaset heir electron donor or acceptor strength with respect to their neutrale quivalents.…”

Section: Introductionmentioning

confidence: 86%

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Efficient Excited‐State Symmetry Breaking in a Cationic Quadrupolar System Bearing Diphenylamino Donors

et al. 2015

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We report a joint experimental and theoretical investigation of a quadrupolar D-π-A(+) -π-D system, the electron donors being diphenylamino groups and the electron acceptor being a methylpyridinium, in comparison with the dipolar D-π-A(+) system. The emission spectra of the two compounds overlap in all the investigated solvents. This finding could be rationalized by TD-DFT calculations: the LUMO-HOMO molecular orbitals involved in the emission transition are localized on the same branch of the quadrupolar structure that becomes the fluorescent portion, corresponding to that of the single-arm compound. Excited-state symmetry breaking has been rarely observed for quadrupolar systems showing negative solvatochromism and is here surprisingly revealed, even in low polarity solvents. Femtosecond transient absorption measurements revealed that an efficient photoinduced intramolecular charge transfer takes place in the quadrupolar chromophore, more efficient than in its dipolar analogue. This result is promising in view of the application of these compounds as novel two-photon absorbing materials.

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Section: Introductionmentioning

confidence: 86%

Section: Introductionmentioning

confidence: 86%

Efficient Excited‐State Symmetry Breaking in a Cationic Quadrupolar System Bearing Diphenylamino Donors

et al. 2015

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“…Another octupolar dye that selectively stains the cytoplasm was reportedb yT ian and co-workers. [24] This dye bears at riphenylamine core and bis-cyano-substituted isophorones as acceptors. The Yang group sensed H 2 Sw ith aC u II -cyclen-substituted triarylborane.…”

Section: Introductionmentioning

confidence: 99%

The Effect of Branching on the One‐ and Two‐Photon Absorption, Cell Viability, and Localization of Cationic Triarylborane Chromophores with Dipolar versus Octupolar Charge Distributions for Cellular Imaging

Griesbeck

Michail

Rauch

et al. 2019

Chemistry A European J

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Twod ifferentchromophores,n amely ad ipolar and an octupolar system,w ere prepared and their linear and nonlinear optical properties as well as their bioimaging capabilities were compared. Both contain triphenylamine as the donor and at riarylboranea st he acceptor, the latter modified with cationic trimethylammonio groups to provide solubility in aqueous media. The octupolar systeme xhibits a much higher two-photon brightness, and also better cell viability and enhanced selectivity for lysosomes comparedw ith the dipolar chromophore. Furthermore, both dyes were applied in two-photon excitedf luorescence( TPEF) live-cell imaging.[**] We are aware that the dipole moment m in our charged compounds is origin-dependenta nd not an observable quantity. [35] For simplification, we use the term dipole moment to describe the electron-density distribution in our chargedc ompounds. Thus,the terms dipole and octupole are used accordingly.Supporting information and the ORCID identification number(s) for the author(s) of this articlecan be found under: https://doi.org/10.

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“…Large Stokes' shifts were observed for chromophores 2, as a consequence of intramolecular charge transfer from the donor to the acceptor moieties after excitation by light. The large Stokes' shift is indicative of a large difference in the spatial arrangement of the chromophore in the absorbing and emitting states, with a consequent increase in the dipole moment and orientational polarizability [21][22].…”

Section: Photophysical Study Of Benzothiazolesmentioning

confidence: 99%

Arylthienyl-vinyl-benzothiazoles as Efficient Second Harmonic Generators (SHG) for Nonlinear Optics

Batista

Costa

Belsley

et al. 2018

22nd International Electronic Conference on Synthetic Organic Chemistry

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New push-pull second harmonic generation (SHG) chromophores 2 were synthesized in order to study their linear and nonlinear optical properties. The donor-acceptor π-conjugated systems 2 were prepared in good to excellent yields by a simple aldol-type condensation of the precursor aldehydes 1 with 6-nitro-2-methyl-1,3-benzothiazole in the presence of NaOH. Hyper-Rayleigh scattering in dioxane solutions was used to evaluate their second-order nonlinear optical properties. The experimental results showed that the optical (linear and nonlinear) properties are influenced by the electron-donor strength of the groups of the π-conjugated bridge. The vinyl-benzothiazole derivative 2b, with methoxyl as the donor group, exhibited the largest first hyperpolarizability β (1660 × 10−30 esu, 40 times greater than the standard reference pNA molecule) and the highest decomposition temperature (Td = 360 °C). The good balance between nonlinearity and thermal stability makes this compound a promising candidate as second harmonic generator (SHG) for nonlinear optics.

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Triphenylamine isophorone derivatives with two photon absorption: Photo-physical property, DFT study and bio-imaging

Cited by 43 publications

References 43 publications

Efficient Excited‐State Symmetry Breaking in a Cationic Quadrupolar System Bearing Diphenylamino Donors

Efficient Excited‐State Symmetry Breaking in a Cationic Quadrupolar System Bearing Diphenylamino Donors

The Effect of Branching on the One‐ and Two‐Photon Absorption, Cell Viability, and Localization of Cationic Triarylborane Chromophores with Dipolar versus Octupolar Charge Distributions for Cellular Imaging

Arylthienyl-vinyl-benzothiazoles as Efficient Second Harmonic Generators (SHG) for Nonlinear Optics

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