X-ray structure determination and analysis of hydrogen interactions in 3, 3′-dimethoxybiphenyl

Rajnikant,; Dinesh, .; Singh, Dara

doi:10.1007/bf02708481

Cited by 3 publications

(1 citation statement)

References 28 publications

(30 reference statements)

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“…This structural parameter is particularly important because it affects each dye molecule’s degree of π conjugation, which will affect its photophysical properties. For the DPA-Ph n -CAA family of molecules (Table S1 in the Supporting Information), we found that their π-spacers ( n > 1) are nonplanar between the two neighboring Ph rings with dihedral angles in the range 30–35° (the average value is 34.1°), which is close to the inter-ring dihedral angle of 37.5° in the crystal structure of 3,3′-dimethoxybiphenyl determined by X-ray diffraction methods . These results indicate the steric repulsion between two neighboring Ph rings.…”

Section: Resultssupporting

confidence: 70%

Spacer Effects of Donor-π Spacer-Acceptor Sensitizers on Photophysical Properties in Dye-Sensitized Solar Cells

et al. 2016

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The donor (D)-π spacer-acceptor (A) framework with electronic push–pull effects provides suitable molecular architectures for molecular design used as efficient light-harvesting sensitizers in dye-sensitized solar cells (DSSCs). Efficiencies of light harvesting and electron injection to the semiconductor of sensitizers play critical roles in DSSC performance. Here, we employed density functional theory to systematically and comparatively investigate the effects of π-spacers of D-π spacer-A types of dyes in solution and adsorbed on a (TiO2)38 anatase cluster on various photophysical properties. The absorption spectra, electron transfer probability, and related photophysical properties of D-π spacer-A types of dyes were investigated as functions of different types (thiophene (Th)- and phenyl (Ph)-based), lengths, and planarity (bridging two neighboring rings; dithieno-thiophene (DTT) and fluorene (FL)-based) of π-spacers, while the D (diphenylamine) and A (cyano-acrylic acid) moieties remained the same. Spacers could significantly influence the λmax values and electron transfer probability. The spacer length has a red-shifted effect in λmax for the Th-, DTT-, and FL-based sensitizers due to their planar conjugated structures; nevertheless, the λmax values are saturated by ring number three. In contrast, the Ph-based spacers induce a blue-shift in λmax with spacer length due to their nonplanar structures. Interestingly, the Th- and DTT-based spacers with lower LUMO energy levels trap more electron density and thus reduce the probability of electron density transfer to TiO2 φET(λmax, TiO2) upon photoexcitation; moreover, the φET(λmax, TiO2) values decrease significantly with ring number. On the other hand, the φET(λmax, TiO2) values for the Ph- and FL-based sensitizers are less sensitive to the spacer length. Interestingly, the orders of theoretical maximum short-circuit current density of four studied families of molecules are correlated with their λmax values. Our study shows the Th–Th motif used as a π-spacer balances the spectral match with solar radiation and φET(λmax, TiO2) suitable for DSSC applications. Our results based on molecular and electronic structures could be used for rational sensitizer design of organic dyes for DSSC applications.

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Section: Resultssupporting

confidence: 70%

Spacer Effects of Donor-π Spacer-Acceptor Sensitizers on Photophysical Properties in Dye-Sensitized Solar Cells

et al. 2016

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Synthesis, crystal structure, quantum chemical computation and molecular docking analysis of 1-(4(tert-butyl)-4-methoxy-[1,1-biphenyl]-4-yl) ethenone

Kumari,

Yadav,

Sankpal

et al. 2024

J IRAN CHEM SOC

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Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl

et al. 2023

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4-(tert-Butyl)-4-nitro-1,1-biphenyl has been synthesized, and its structure has been characterized by using some spectroscopic and single-crystal X-ray diffraction techniques. It crystallizes in a monoclinic crystal system with space group P21/n and unit cell parameters: a = 6.4478(3) Å, b = 9.2477(4) Å, c = 23.4572(9) Å, β = 95.114(4)°, V = 1393.11(10) Å3, Z = 4. The molecular structure has been solved by using the intrinsic phasing method. The crystal structure is stabilized by C-H···O interactions. Computational studies were performed using density functional theory (DFT) and Hartree-Fock (HF) methods. The optimized geometry obtained from DFT and HF in the gas phase was compared with solid-phase experimental data retrieved from single-crystal X-ray diffraction results. Frontier molecular orbitals, such as the HOMO/LUMO energy gap, the molecular electrostatic potential, and Mulliken atomic charges, have been investigated. The HOMO LUMO energy gap of 3.97 eV indicates that the molecule is soft and highly reactive. The Hirshfeld surface analysis and their associated fingerprint plots have been used to quantitatively validate the interactions. Further insilico molecular docking studies have been performed with the molecular target Type-II topoisomerase (PDB ID: 1JIJ) and their results suggest that 4-(tert-butyl)-4-nitro-1,1-biphenyl could be considered an anticancer drug.

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X-ray structure determination and analysis of hydrogen interactions in 3, 3′-dimethoxybiphenyl

Cited by 3 publications

References 28 publications

Spacer Effects of Donor-π Spacer-Acceptor Sensitizers on Photophysical Properties in Dye-Sensitized Solar Cells

Spacer Effects of Donor-π Spacer-Acceptor Sensitizers on Photophysical Properties in Dye-Sensitized Solar Cells

Synthesis, crystal structure, quantum chemical computation and molecular docking analysis of 1-(4(tert-butyl)-4-methoxy-[1,1-biphenyl]-4-yl) ethenone

Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl

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