First hyperpolarizability of some nonconjugated donor–acceptor 3D molecules: noncentrosymmetric crystal through conformational flexibility

Srinivas, K.; Sitha, Sanyasi; Rao, V. Jayathirtha; Bhanuprakash, K.; Ravikumar, K.; Anthony, Savarimuthu Philip; Radhakrishnan, T. P.

doi:10.1039/b414311f

Cited by 31 publications

(24 citation statements)

References 78 publications

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“…other end of the aromatic ring is donated to the pyramidal nitrogen of a neighbouring -NH 2 , leaving the second hydrogen to be perforce donated to fluorine. In NAJJOY (Srinivas et al, 2005), there are three N-H donors and three triazine nitrogens. However, one of the ring nitrogens is flanked by fluorobenzyl groups and is difficult to approach closely; unsurprisingly, it does not accept.…”

Section: Short X-há á áF-c Hydrogen Bondsmentioning

confidence: 99%

The hydrogen bond between N—H or O—H and organic fluorine: favourable yes, competitive no

Taylor

2017

Acta Crystallogr Sect B

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A study was made of X-H...F-C interactions (X = N or O) in small-molecule crystal structures. It was primarily based on 6728 structures containing X-H and C-F and no atom heavier than chlorine. Of the 28 451 C-F moieties in these structures, 1051 interact with X-H groups. However, over three-quarters of these interactions are either the weaker components of bifurcated hydrogen bonds (so likely to be incidental contacts) or occur in structures where there is a clear insufficiency of good hydrogen-bond acceptors such as oxygen, nitrogen or halide. In structures where good acceptors are entirely absent, there is about a 2 in 3 chance that a given X-H group will donate to fluorine. Viable alternatives are X-H...π hydrogen bonds (especially to electron-rich aromatics) and dihydrogen bonds. The average H...F distances of X-H...F-C interactions are significantly shorter for CRF (R = C or H) and Csp-F acceptors than for CRF. The X-H...F angle distribution is consistent with a weak energetic preference for linearity, but that of H...F-C suggests a flat energy profile in the range 100-180°. X-H...F-C interactions are more likely when the acceptor is Csp-F or CRF, and when the donor is C-NH. They also occur significantly more often in structures containing tertiary alcohols or solvent molecules, or with Z' > 1, i.e. when there may be unusual packing problems. It is extremely rare to find X-H...F-C interactions in structures where there are several unused good acceptors. When it does happen, there is often a clear reason, e.g. awkwardly shaped molecules whose packing isolates a donor group from the good acceptors.

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Section: Short X-há á áF-c Hydrogen Bondsmentioning

confidence: 99%

The hydrogen bond between N—H or O—H and organic fluorine: favourable yes, competitive no

Taylor

2017

Acta Crystallogr Sect B

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“…Schuddeboom et al [17] have measured the hyperpolarizability values of nonconjugatively linked donor-acceptor compounds in which a rigid, saturated hydrocarbon bridge separates D (donator) and A (acceptor) groups by at least three -bonds. Bhanuprakash and coworkers [18,19] have studied the NLO activity in some nonconjugated 3D triazine derivatives from both experiment and theoretical calculation. Moreover, Bhanuprakash and coworkers [20] systematically studied the role of orbital interactions through -bonds on enhanced NLO response in zwitterionic molecules.…”

Section: Introductionmentioning

confidence: 99%

Theoretical study on the second‐order nonlinear optical properties of nonconjugated D‐π‐A chromophores

Yang¹,

Su²

2009

Int J of Quantum Chemistry

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Density functional theory calculations have been carried out on nonconjugated D--A chromophores to investigate the different electron donors and conjugated bridges effects on the molecular nonlinear optical response. The results show that the large second-order polarizability values can be achieved through careful combination of available electron donors, conjugated bridges for our studied nonconjugated D--A chromophores. The calculations also provide a clear explanation for the second-order polarizability changes from the standpoint of transition energies, oscillator strengths, electron density difference, and bond length alternation. Solvent effect has great influence on the second-order polarizability and electronic absorption spectrum. It is hoped that the results presented in this article will give some hints to the interrelated studies.

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“…In this case, the OH group acts as a disabling or metamanager. The values of in chloroform are 3 to 5 times higher than the 2,4,6-tris(benzylamino)-1,3,5triazine [24] derivatives also measured in chloroform. Figure 10 shows the shape index surface for the EPAF, where it is possible to see two triangles, one blue and the other red, one facing the other, representing the -interaction ( ... = 3,779Å).…”

Section: And 5(d))mentioning

confidence: 58%

Prediction of the Linear and Nonlinear Optical Properties of a Schiff Base Derivatives via DFT

Valverde

Ribeiro

Soares

et al. 2019

Advances in Condensed Matter Physics

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In this work, the density functional theory (DFT) calculation combined with a polarizable continuum model (PCM) was used to study the solvent media effects on the electrical and geometrical behaviors of the Schiff-base derivative, (E)-4-[({4-[(pyridin-2-ilmetilideno)amino]phenyl}amino)-metil]fenol (EPAF). The linear and nonlinear optics parameters, as the dipole moment, linear polarizability, and first and second hyperpolarizabilities, were calculated at DFT/B3LYP/6-311+G(d) level, for the EPAF molecule in several solvent media. The dynamic behavior of the Hyper-Rayleigh Scattering (HRS) first hyperpolarizability was studied as function of the electric field frequency. The results presented for HRS first hyperpolarizability suggest that the studied crystal has good nonlinear optical properties. In addition, the gap energy was calculated from the HOMO-LUMO energies difference in several solvent media. The EPAF crystal intermolecular interactions were studied by the Hirshfeld surface analysis. The third-order electric susceptibility χ(3) of the crystal EPAF was also calculated, indicating the EPAF crystal as a promising candidate for NLO applications in photonic and optoelectronic devices.

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First hyperpolarizability of some nonconjugated donor–acceptor 3D molecules: noncentrosymmetric crystal through conformational flexibility

Cited by 31 publications

References 78 publications

The hydrogen bond between N—H or O—H and organic fluorine: favourable yes, competitive no

The hydrogen bond between N—H or O—H and organic fluorine: favourable yes, competitive no

Theoretical study on the second‐order nonlinear optical properties of nonconjugated D‐π‐A chromophores

Prediction of the Linear and Nonlinear Optical Properties of a Schiff Base Derivatives via DFT

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