Two-photon resonant hyperpolarizability of an H-shaped molecule studied by wavelength-tunable hyper-Rayleigh scattering

Zhu, Jun‐Jie; Lu, Can‐Zhong; Cui, Yiping; Zhang, Chaozhi; Lu, Guo‐ping

doi:10.1063/1.3506421

Cited by 9 publications

(3 citation statements)

References 54 publications

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“…The standard reaction conditions (1,4-dioxane/K 2 CO 3 ) were slightly modified, as a small amount of acetonitrile was added to provide better solubility of the dicyanonaphthalene precursor. Pd(PPh 3 ) 2 Cl 2 as catalyst instead of Pd 0 salts allowed us to shorten the reaction time from 13 to 6 h [48][49][50][51][52]. All compounds were characterized by nuclear magnetic resonance spectroscopy (NMR, Supporting Information File 1, Figures S1-S24) as well as exact electrospray mass spectrometry (EM-ESIMS, Supporting Information File 1, Figures S25-S30) and appear as white to faint yellow solids.…”

Section: Synthesis and Structural Characterizationmentioning

confidence: 99%

Naphthalonitriles featuring efficient emission in solution and in the solid state

Sailaja¹,

Maisuls²,

Kösters³

et al. 2020

Beilstein J. Org. Chem.

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In this work, a series of γ-substituted diphenylnaphthalonitriles were synthesized and characterized. They show efficient emission in solution and in the aggregated state and their environment responsiveness is based on having variable substituents at the para-position of the two phenyl moieties. The excited state properties were fully investigated in tetrahydrofuran (THF) solutions and in THF/H2O mixtures. The size of the aggregates in aqueous media were measured by dynamic light scattering (DLS). The steady-state and time-resolved photoluminescence spectroscopy studies revealed that all the molecules show intense fluorescence both in solution and in the aggregated state. In THF solutions, a blue emission was observed for the unsubstituted (H), methyl- (Me) and tert-butyl- (t-Bu) substituted γ-diphenylnaphthalonitriles, which can be attributed to a weak π-donor capability of these groups. On the other hand, the methoxy- (OMe), methylsulfanyl- (SMe) and dimethylamino- (NMe2) substituted compounds exhibit a progressive red-shift in emission compared to H, Me and t-Bu due to a growing π-electron donating capability. Interestingly, upon aggregation in water-containing media, H, Me and t-Bu show a slight red-shift of the emission and a blue-shift is observed for OMe, SMe and NMe2. The crystal structure of Me allowed a detailed discussion of the structure–property relationship. Clearly, N-containing substituents such as NMe2 possess more electron-donating ability than the S-based moieties such as SMe. Moreover, it was found that NMe2 showed higher luminescence quantum yields (ΦF) in comparison to SMe, indicating that N-substituted groups could enhance the fluorescence intensity. Therefore, the π-donor nature of the substituents on the phenyl ring constitutes the main parameter that influences the photophysical properties, such as excited state lifetimes and photoluminescence quantum yields. Hence, a series of highly luminescent materials from deep blue to red emission depending on substitution and environment is reported with potential applications in sensing, bioimaging and optoelectronics.

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Section: Synthesis and Structural Characterizationmentioning

confidence: 99%

Naphthalonitriles featuring efficient emission in solution and in the solid state

Sailaja¹,

Maisuls²,

Kösters³

et al. 2020

Beilstein J. Org. Chem.

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“…Hyper-Rayleigh scattering (HRS) is second-harmonic light scattering mediated by the molecular first hyperpolarizability β, and HRS is widely employed to measure β of organic chromophores in solution. [1][2][3][4][5][6][7][8] It is usually assumed that the molecules are independent and randomly oriented, so that the observed HRS signal from the sample is the result of incoherent addition of HRS from each individual molecule. Tensor components of β are obtained from experimental measurements of the HRS intensity and its polarization dependence.…”

Section: Introductionmentioning

confidence: 99%

“…10,11 Recent work has also addressed the need to measure the frequency dependence of β by developing apparatus which combines broad spectral tunability of the input laser and spectral analysis of the HRS light. 7,8 The present apparatus was developed to enable very accurate HRS polarization measurements with linear polarized light at or near the 90 • scattering geometry. The motivation for such measurements is the finding that the polarization and angular dependence of HRS from some molecular liquids is inconsistent with the assumption of independent randomly oriented molecules.…”

Section: Introductionmentioning

confidence: 99%

Accurate hyper-Rayleigh scattering polarization measurements

Shelton

2011

Review of Scientific Instruments

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Apparatus and methods are described for measurement of the polarization dependence of hyper-Rayleigh scattering near 90° scattering angle with 0.1% accuracy for all four configurations where the incident and scattered light is linear polarized either parallel or perpendicular to the scattering plane. Measurements are made with large collection aperture and extrapolated to zero collection numerical aperture (NA = 0). Fiber coupling allows the system to be easily reconfigured for either polarization or spectral measurements.

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T‐Shaped (Donor–π–)₂Acceptor–π–Donor Push–Pull Systems Based on Indan‐1,3‐dione

et al. 2015

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Sixteen model (donor-π-) 2 acceptor-π-donor [(D-π-) 2 A-π-D] molecules with an extraordinary T-shaped arrangement were designed and synthesized. Indan-1,3-dione was employed as a central acceptor with electron donors linked at the C-2, C-4, and C-7 positions. These push-pull molecules represent a first systematic modification of an indan-1,3-dione-fused benzene ring. The structures and properties of all target molecules were investigated by X-ray analysis, electrochemistry, UV/Vis absorption spectroscopy, differential scanning calorimetry, electric-field-induced second-harmonic generation (EFISHG) studies, and DFT calculations. A thorough evaluation of all of the gathered data has been performed,

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Two-photon resonant hyperpolarizability of an H-shaped molecule studied by wavelength-tunable hyper-Rayleigh scattering

Cited by 9 publications

References 54 publications

Naphthalonitriles featuring efficient emission in solution and in the solid state

Naphthalonitriles featuring efficient emission in solution and in the solid state

Accurate hyper-Rayleigh scattering polarization measurements

T‐Shaped (Donor–π–)₂Acceptor–π–Donor Push–Pull Systems Based on Indan‐1,3‐dione

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Two-photon resonant hyperpolarizability of an H-shaped molecule studied by wavelength-tunable hyper-Rayleigh scattering

Cited by 9 publications

References 54 publications

Naphthalonitriles featuring efficient emission in solution and in the solid state

Naphthalonitriles featuring efficient emission in solution and in the solid state

Accurate hyper-Rayleigh scattering polarization measurements

T‐Shaped (Donor–π–)2Acceptor–π–Donor Push–Pull Systems Based on Indan‐1,3‐dione

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Product

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T‐Shaped (Donor–π–)₂Acceptor–π–Donor Push–Pull Systems Based on Indan‐1,3‐dione