Improved Nonlinearity–Transparency–Thermal Stability Trade-Off with Spirobifluorene-Bridged Donor-π-Acceptor Chromophores

Xiao, Haibo; Yin, Hongyao; Zhang, Xiaoying

doi:10.1021/ol302443z

Cited by 20 publications

(11 citation statements)

References 30 publications

(31 reference statements)

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“…The spirobifluorene acted as a π-conjugated bridge because of the presence of the spiroconjugation effect between the electron acceptor and the donor. [94] Compared to the values in Huang et al, [90,92] molecules with dicyanomethylene and nitrophenyl groups showed TPA cross-sections www.advopticalmat.de s of 2928 and 3773 GM, respectively. The compound with the cyano group demonstrated more than an order of magnitude increase of the TPA cross-section with s = 62 949 GM.…”

Section: Optimization Of Hyperpolarizability In Individual Moleculesmentioning

confidence: 69%

“…The compound with the cyano group demonstrated more than an order of magnitude increase of the TPA cross-section with s = 62 949 GM. [94] These examples suggest promising strategies to improve the NLO properties of individual molecules (see Table 1 for a summary of the optical properties of the discussed molecules), yet optimal crystallization routes which would allow to obtain molecular crystals based on molecules with a spirobifluorene core yet have to be developed.…”

Section: Optimization Of Hyperpolarizability In Individual Moleculesmentioning

confidence: 99%

“…While excited along the crystallographic c-axis (parallel to the substrate), the SHG emitted from the DPFO microfiber in transmission gave an extremely high polarization ratio ρ = (I max − I min )/(I max + I min ) of 0.997 ± 0.02, which is higher than for most of the reported organic crystals. [97] In particular, the results of polarization dependent measurements suggest Huang et al [92] F-FO-F a) 392 570 5618 0.76 626 Huang et al [90] TPA-FO-TPA a) 409 597 5319 1.07 884 Huang et al [90] P-F-FO-F-P a) 423 571 6128 2.11 1743 Huang et al [92] Acceptor: cyano group 368 62 949 Xiao et al [94] Acceptor: dicyanomethylene group 376 2928 Xiao et al [94] Acceptor; nitrophenyl group 378 3773 Xiao et al [94] All the data were measured in solution. a) Fluorenone (FO) was used as core and three different donors were added: phenothiazine(P), fluorene (F), and triphenylamine (TPA).…”

Section: Dpfomentioning

confidence: 99%

See 2 more Smart Citations

Nonlinear Optical Properties and Applications of Fluorenone Molecular Materials

Semin

Duan

et al. 2021

Advanced Optical Materials

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Fluorenone molecular materials provide an excellent platform to engineer new materials that are very promising for photonic and optoelectronic applications, such as very efficient optical second harmonic (SHG) and terahertz (THz) generation, light emitting diodes, biomarkers, solar cells, and sensors. More recently, there have been a lot of research efforts dedicated towards the nonlinear optical (NLO) properties of these fluorenone materials because of their unique combination of chemical, structural, and optical properties. This review addresses the state of the art of this very interesting and potent class of molecular materials. In particular, the NLO susceptibilities, their potential for optical SHG and THz generation and their two‐photon luminescence properties and how to optimize these by rational design are reviewed. Flexibility and easiness of modification of their molecular properties combined with their structural polymorphism enable a variety of applications. Perspectives and future research directions for these fluorenone materials are also presented.

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Section: Optimization Of Hyperpolarizability In Individual Moleculesmentioning

confidence: 69%

Section: Optimization Of Hyperpolarizability In Individual Moleculesmentioning

confidence: 99%

Section: Dpfomentioning

confidence: 99%

See 1 more Smart Citation

Nonlinear Optical Properties and Applications of Fluorenone Molecular Materials

Semin

Duan

et al. 2021

Advanced Optical Materials

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“…As a consequence, a large number of chromophores have been designed with high b values and good transparency. [7][8][9][10][11] However, defeating the nonlinearity-transparency trade-off is still a major challenge.…”

Section: Introductionmentioning

confidence: 99%

Novel NLO-phores containing dihexyl amino benzo[b]thiophene exhibiting good transparency and enhanced electro-optical activity

Zhang

Peng

et al. 2014

RSC Adv.

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Two new chromophores (A and B) were synthesized, in which a benzo [b]thiophene moiety was first introduced as a donor group. To investigate the macroscopic EO activity of the new chromophores, guest-host doped polymer films were fabricated by doping chromophores A and B into amorphous polycarbonate (APC). The poled films containing A with a loading density of 20 wt% achieved a maximum EO coefficient (r 33 ) of 42 pm V À1 at 1310 nm, while for the poled films containing B, the r 33 value is 75 pm V À1 at 1310 nm. UV-vis spectral absorption of the new chromophores were studied in solutions and films, and chromophores A and B showed a maximum absorption in chloroform of 658 nm and 688 nm, respectively. Compared to the FTC (r 33 ¼ 20-50 pm V À1 at 1310 nm, l max ¼ 685 nm in chloroform) analogues, they exhibited enhanced electro-optical activity together with a high optical gap.This new type of chromophore provided better optimization of the nonlinearity-transparency trade-off.

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“…Nonlinear optical (NLO) properties of materials have been widely investigated due to potential applications in various fields such as data storage, communication and information processing [1][2][3][4]. Many organic donor-p-acceptor (D-p-A) compounds have been the focus of sizeable research efforts [5,6].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and optical properties of a D–A–D cationic cyclopentadienyl iron complex containing double arylazo chromophores

Liu

Jia

Li³

et al. 2014

Res Chem Intermed

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A D-A-D cationic cyclopentadienyl iron complex containing double arylazo chromophores (Fc-diazo) with methoxyl group (Fc-diazo-OMe) was obtained via nucleophilic substitution and well characterized by IR, UV-visible, 1 H NMR, and 13 C NMR spectroscopy, and MS. UV-Vis absorption and nonlinear optical property of Fc-diazo-OMe were investigated by comparison of Fc-diazo with no methoxyl group (Fc-diazo-H). Quantum chemical calculations of the orbital energy, geometric structure of Fc-diazo-OMe, and Fc-diazo-H were conducted by using density functional methods at the B3PW91/Lanl2dz level. Charge transfer from the highest occupied molecular orbital to the lowest unoccupied molecular orbital was found based on density functional theory. The substitution of the methoxyl group greatly improves the NLO property of Fc-diazo. Fc-diazo-OMe shows effective two-photon absorption, coefficient and third-order nonlinear susceptibility for potential applications as optical materials, while Fc-diazo-H barely shows NLO ability.

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Improved Nonlinearity–Transparency–Thermal Stability Trade-Off with Spirobifluorene-Bridged Donor-π-Acceptor Chromophores

Cited by 20 publications

References 30 publications

Nonlinear Optical Properties and Applications of Fluorenone Molecular Materials

Nonlinear Optical Properties and Applications of Fluorenone Molecular Materials

Novel NLO-phores containing dihexyl amino benzo[b]thiophene exhibiting good transparency and enhanced electro-optical activity

Synthesis and optical properties of a D–A–D cationic cyclopentadienyl iron complex containing double arylazo chromophores

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