Theoretical Study on the Chiroptical Optical Properties of Chiral Fullerene C<sub>60</sub>Derivative

Yang, Guochun; Si, Yanling; Su, Zhong‐Min

doi:10.1021/jp204860x

Cited by 28 publications

(17 citation statements)

References 86 publications

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“…In all cases, frequency calculations were performed in order to confirm the nature of the stationary points (minima with no imaginary frequency). The UV-Vis parameters (maximum wavelength, electronic excitation energies, and oscillator strengths) of the studied compounds have been calculated with the time-dependent density functional theory (TD-B3LYP) at the 6-31G(d) level of theory [53,54] in order to evaluate the sensing effect made by CN − ion. All the detailed calculations were carried out through the facilities provided by the Gaussian09 package [55].…”

Section: Computational Detailsmentioning

confidence: 99%

A new phenothiazine-based selective visual and fluorescent sensor for cyanide

et al. 2020

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A new donor-π-acceptor derived from phenothiazine, namely 2-(2-((10-hexyl-10H-phenothiazin-3-yl)methylene)-3-oxo-2,3-dihydroinden-1-ylidene) malononitrile (PTZON) was synthesized and fully characterized, and its potential as a fluorescent sensor for cyanide anion was investigated. The PTZON showed a visible absorption band at 564 nm corresponds to an intramolecular charge transfer (ICT) and an emission band at 589 nm in CH 3 CN/H 2 O. The results of cyanide anion titration revealed ratiometric changes in both absorption and fluorescence spectra as a result of the nucleophilic addition of cyanide anion via Michael addition. The optical studies, FT-IR spectra, NMR, high-resolution mass, and DFT calculations confirmed the sensing mechanism. The selectivity of PTZON as a cyanide anion fluorescent sensor was proved in mixed solvent solutions, and the sensitivity was as low as 0.011 µM, which is far lower than the value allowed by the United States Environmental Protection Agency for drinking water (1.9 µM). Also, the detection limit of PTZON was assessed to be 3.39 μM by the spectrophotometric method. The binding stoichiometry between PTZON and cyanide anion was found to be 1:1 as evidenced by mass spectra. TLC silica-coated plates test strips demonstrated the fluorescent detection of cyanide anion.

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Section: Computational Detailsmentioning

confidence: 99%

A new phenothiazine-based selective visual and fluorescent sensor for cyanide

et al. 2020

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“…The UV-Vis parameters (maximum wavelength, electronic excitation energies and oscillator strengths) of the studied compounds have been calculated at the TD-B3LYP/6-31G(d) level of theory. 17,18 For the comparison with C 60 and the mono-adduct, we used B3LYP/6-31++G(d,p) to determine the HOMO, LUMO and the energy gap for these systems.…”

Section: Computational Detailsmentioning

confidence: 99%

Theoretical study of bis-adduct fulleropyrrolidines isomers

Khemiri¹,

Milad²,

Jedidi³

et al. 2019

Rev.Roum.Chim.

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A detailed theoretical investigation of bis-adduct fulleropyrrolidines was developed in our work. All the possible isomers of our molecule were determined. Corresponding structures were optimized, their energies were calculated and their stability was discussed using the density functional theory method. The theoretical calculation carried out in our work shows that the trans and equatorial structures of the bis adduct are the most stable structures among the eight different possible isomers. The LUMO energy calculated for the bis adduct shows that it is higher than the LUMO of C60 and the LUMO of the mono adduct calculated at the same level. This suggests that this compound can be used efficiently as electron acceptor in photovoltaic cell application.

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“…2 along with the experimental spectra. 107 The geometries of the studied compounds are re-optimized to test the influence of THF solvent under the PCM model. Moreover, the values of the rotational strengths calculated using the length and velocity gauge representation of the electric dipole operator are close to each other.…”

Section: Uv-vis and CD Spectramentioning

confidence: 99%

Photophysical properties of quinoxaline-fused [7]carbohelicene derivatives

Liu

Pan

et al. 2015

RSC Adv.

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Helicene and its derivatives have received much attention as the candidates of organic photoelectronic material. Recently, novel quinoxaline-fused [7]carbohelicene derivatives exhibit unique structural and photophysical properties, especially in the crystal states. However, their structure-property relationships have not been fully understood from the micromechanism, which is also important to further improve their performance. Here, the electronic transition, electronic circular dichroism (CD), second-order nonlinear optical (NLO) response and charge transport properties of five quinoxaline-fused [7]carbohelicene derivatives have been investigated based on density functional theory calculations. The experimental UV-Vis/CD spectra of the studied compounds were well reproduced by our calculations. Thus, we can assign their electron transition properties and absolution configurations (ACs) with high confidence. It is found that CD bands of quinoxaline-fused [7]carbohelicene derivatives mainly originate from exciton coupling between quinoxaline, phenyl or 4-methoxyphenyl and [7]carbohelicene, which is in sharp contrast to [7]carbohelicene. More interestingly, these derivatives possess large first hyperpolarizability values. For example, the βHRS value of compound 6 is 32.96 × 10 −30 esu, which is about 190 times larger than that of the organic urea molecule. The bandwidth of valence band of compound 2 is comparable to that of conduction band and slightly larger than that of tris(8-hydroxyquinolinato)aluminium. This means that compound 2 is the potential candidate as ambipolar charge transport material. Please do not adjust marginsPlease do not adjust margins modulates the LUMO energy level. As a consequence, LUMO energy of compound 2 is much lower than that of compound 1 (Table S6), which leads to the smaller energy gap (Eg) for compound 2. Moreover, the main electron transitions characters are of charge transfer from quinoxaline to [7]carbohelicene and vice versa (Fig. 3). On the basis of above analysis, it is found that involvement of quinoxaline unit not only modulates the electron absorption wavelength but also alter the electron transition property. Compounds 3 and 4 also exhibit four absorption bands, which is similar to those of compound 2. In other words, the substituent effect of phenyl or 4-methoxyphenyl group on the UV-Vis spectra of compound 2 is not great. It is noted that some of the molecular orbitals involved in these transitions partially located on the phenyl or 4-methoxyphenyl group. Fig. 2Calculated UV-Vis (left) and CD (right) spectra in gas phase of 1, 2, 3 and 4 at the TDB3LYP/6-31+G(d) level of theory along with the experimental spectra (red dashed line).

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Theoretical Study on the Chiroptical Optical Properties of Chiral Fullerene C₆₀Derivative

Cited by 28 publications

References 86 publications

A new phenothiazine-based selective visual and fluorescent sensor for cyanide

A new phenothiazine-based selective visual and fluorescent sensor for cyanide

Theoretical study of bis-adduct fulleropyrrolidines isomers

Photophysical properties of quinoxaline-fused [7]carbohelicene derivatives

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Theoretical Study on the Chiroptical Optical Properties of Chiral Fullerene C60Derivative

Cited by 28 publications

References 86 publications

A new phenothiazine-based selective visual and fluorescent sensor for cyanide

A new phenothiazine-based selective visual and fluorescent sensor for cyanide

Theoretical study of bis-adduct fulleropyrrolidines isomers

Photophysical properties of quinoxaline-fused [7]carbohelicene derivatives

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Theoretical Study on the Chiroptical Optical Properties of Chiral Fullerene C₆₀Derivative