Toward First-Principles Design of Organic Nonlinear Optical Materials: Crystal Structure Prediction and Halogen Bonding Impact on Hyperpolarizabilities of 2-Iodo-3-hydroxypyridine

Yushina, I. D.; Masunov, Artëm E.; López, Diana; Dyakov, Alexander A.; Барташевич, Е. В.

doi:10.1021/acs.cgd.8b00529

Cited by 25 publications

(14 citation statements)

References 90 publications

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“…Here, 4.35 is the vdW diameter in Å, and 0.50 is the depth of vdW minimum in kcal/mol. These parameters had been recently validated in the CSP of another noncentrosymmetric NLO material …”

Section: Resultsmentioning

confidence: 99%

“…We used the predicted polymorphic structures to compare the angular distributions of the intermolecular I···I contacts found in these structures with that found for the fragment C(sp 2 )–I···I–C(sp 2 ) in Cambridge Structural Database . The ∠C–I···I angles were labeled θ 1 and θ 2 (θ 1 > θ 2 ), and the contact asymmetry parameter was defined as |θ 1 – θ 2 |.…”

Section: Resultsmentioning

confidence: 99%

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First-Principles Crystal Engineering of Nonlinear Optical Materials. II. Effect of Halogen Bonds on the Structure and Properties of Triiodobenzenes

et al. 2018

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Recently, we proposed a computational design strategy for organic nonlinear optical materials, based on the global minimization of lattice energy to predict the crystal packing from the first principles. Here, we validate this strategy on triiodobenzenes, which include CH···I hydrogen and I···I halogen bonding as the structure-determining components of their intermolecular interactions. To refine the van der Waals (vdW) parameters for an I atom, the ab initio potential surfaces for the model dimers were calculated at the CCSD(T)/cc-pVTZ + CP theory level. The hydrogen bond C–H···I was found to have an interaction energy of −0.5 kcal/mol. The I···I contact of type I (140°–140°) was found to be attractive with a well depth of −0.4 kcal/mol at a 4.6 Å distance, whereas type II contact (180°–90°) was found to be nearly twice more attractive. Its potential well depth reaches −0.7 kcal/mol at an I···I distance of 4.4 Å. These binding energies are therefore weaker than that of the typical hydrogen bonds. The AMOEBA force-field vdW parameters were fit to describe these interactions and used to predict the crystal structures. Our structure prediction, followed by density functional theorymany-body dispersion ranking established the noncentrosymmetric crystal packing to be the global minimum, in agreement with the experimental data. The coupled perturbed Kohn–Sham approach was used to estimate nonlinear susceptibility, and the predicted values were compared to that of the urea standard. The statistical analysis of the angular distribution for the I···I contacts in the predicted virtual polymorphs was compared to that found among the experimental crystal structures of iodoaromatic compounds. In both cases, symmetric (type I) contacts dominate for shorter and longer I···I distances, whereas L-shaped (type II) contacts are preferred for intermediate distances.

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“…Here, 4.35 is the vdW diameter in Å, and 0.50 is the depth of vdW minimum in kcal/mol. These parameters had been recently validated in the CSP of another noncentrosymmetric NLO material …”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

First-Principles Crystal Engineering of Nonlinear Optical Materials. II. Effect of Halogen Bonds on the Structure and Properties of Triiodobenzenes

et al. 2018

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“…Many research groups, − including ours, − have demonstrated how density functional theory (DFT) in conjunction with global minimization methods for the lattice energy may serve as powerful tools in crystal structure predictions (CSP). The latter include evolutionary algorithms implemented in USPEX .…”

Section: Introductionmentioning

confidence: 99%

Virtual Tensile Test for Brittle, Plastic, and Elastic Polymorphs of 4-Bromophenyl 4-Bromobenzoate

Masunov

Wiratmo

Dyakov

et al. 2020

Crystal Growth & Design

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We report on the development of a novel methodology for computational predictions of the mechanical properties for single crystals. This methodology is based on constrained optimization using dispersion-corrected density functional theory level, and can be dubbed the virtual tensile test. The approach was validated on the example of 4-bromophenyl 4-bromobenzoate, an organic compound known to form three polymorphs with different mechanical characteristics. Each one of these polymorphic crystal structures was stretched stepwise along each crystallographic axis, while the remaining lattice parameters and atomic coordinates were relaxed. The geometrical properties of halogen bonds and the other noncovalent interactions were monitored at each step to understand the nature of mechanical response. The unit cell volumes and lattice energies were plotted as functions of the stretching parameter, and these curves were analyzed in terms of mechanical properties of the brittle, plastic, and elastic polymorphs.

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“…To develop predictive design principles for constructing halogen bonded organic non‐linear optical materials, Bartashevich and co‐workers have done computational studies on 2‐iodo‐3‐hydroxypyridine and predicted its crystal structure that exhibited second harmonic generation intensity [126] . Their studies revealed that I⋅⋅⋅I Type II halogen bonding plays a critical role in generating NLO properties in 2‐iodo‐3‐hydroxypyridine crystal by facilitating noncentrosymmetric molecular packing and polarizing the iodine‐atom.…”

Section: Halogen Bonded Supramolecular Polymers and Materialsmentioning

confidence: 99%

Recent Developments in Polymeric Assemblies and Functional Materials by Halogen Bonding

Biswas

Das

2021

ChemNanoMat

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Polymers have long been known to us for their versatile utility in our daily lives. With many years of successful advancement in controlled polymer synthesis and supramolecular chemistry, currently an amalgamation of these two fields is becoming increasingly important for generating modern‐day emerging polymeric materials. Hydrogen bonding and other noncovalent interactions like π‐stacking, host‐guest interaction, electrostatic interaction, metal‐ligand coordination have been explored much to this context, unlike the recently emerged halogen bonding, which indeed shows advantageous features like superior hydrophobicity, directionality and polar solvent resistance compared to ubiquitous hydrogen bonding. Hence, rendering these properties of halogen bonding into polymeric domain for generating functional materials for application in advance nanotechnologies is highly desirable. In the recent years, substantial progress has been made in fulfilling this challenging goal. This is evident from the escalating number of scientific publications in this research area every year. In this minireview, we have summarized the most recent developments in the field of halogen bonded polymeric assemblies and supramolecular polymers and discussed them in the context of their emerging materials properties and functions. Emphasis is given on highlighting various design criteria adopted in crystal engineering, covalent and supramolecular polymers in the past five years for constructing diverse organic functional materials, viz. liquid crystals, photoresponsive and photochromic materials, biomaterials and gels, self‐healing materials and many others by virtue of this highly directional supramolecular tool. In conclusion, a brief perspective on the advantages, challenges and future prospects in this rapidly growing field of research is discussed.

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Toward First-Principles Design of Organic Nonlinear Optical Materials: Crystal Structure Prediction and Halogen Bonding Impact on Hyperpolarizabilities of 2-Iodo-3-hydroxypyridine

Cited by 25 publications

References 90 publications

First-Principles Crystal Engineering of Nonlinear Optical Materials. II. Effect of Halogen Bonds on the Structure and Properties of Triiodobenzenes

First-Principles Crystal Engineering of Nonlinear Optical Materials. II. Effect of Halogen Bonds on the Structure and Properties of Triiodobenzenes

Virtual Tensile Test for Brittle, Plastic, and Elastic Polymorphs of 4-Bromophenyl 4-Bromobenzoate

Recent Developments in Polymeric Assemblies and Functional Materials by Halogen Bonding

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