New 4-(2-(4-alkoxyphenyl)-6-methoxypyridin-4-yl)benzonitriles: synthesis, liquid crystalline behavior and photo physical properties

Ahipa, T.N.; Kumar, Vijith; Rao, D. S. Shankar; Prasad, S. Krishna; Adhikari, Airody Vasudeva

doi:10.1039/c4ce00128a

Cited by 20 publications

(8 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Moreover, Mps1 inhibitors containing pyrimidine and pyrazole are another examples of the reported Mps1 inhibitors . Synthesis and characterization of some compounds of including 2‐methoxynicotinonitrile have been reported in the literature …”

Section: Introductionmentioning

confidence: 99%

Hirshfeld Surface, Molecular Docking Study, Spectroscopic Characterization and NLO Profile of 2‐Methoxy‐4,6‐Diphenylnicotinonitrile

et al. 2019

View full text Add to dashboard Cite

The compound 2‐methoxy‐4,6‐diphenylnicotinonitrile was characterized by using experimental FT‐IR, Laser‐Raman, 1H and 13C NMR spectra and UV‐Vis. spectroscopic analysis methods. To support experimental structural, vibrational, chemical shift and electronic records, the theoretical analyses were performed at the DFT/B3LYP method with the 6–311++G(2d,2p) basis set. The π⋅⋅⋅π, N⋅⋅⋅π, N⋅⋅⋅H, C⋅⋅⋅H and O⋅⋅⋅H interactions within crystal packing of the compound, which aren't taken into account within the experimental single crystal X‐Ray diffraction study, were investigated in detail with Hirshfeld surface analyses and their related 2D fingerprint plots. The highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO) and their associated parameters were used to explain intra‐molecular charge transfer and global reactivity properties of the compound with the computational level of theory. Non‐linear optical (NLO) profile of the title compound including π electron systems such as aromatic and cyano groups was determined by considering the static polarizability (α) and the static first‐order hyperpolarizability (β) values. Molecular docking analysis was performed to determine intermolecular interactions between a Mps1/TTK protein kinase inhibitor with the title compound.

show abstract

Section: Introductionmentioning

confidence: 99%

Hirshfeld Surface, Molecular Docking Study, Spectroscopic Characterization and NLO Profile of 2‐Methoxy‐4,6‐Diphenylnicotinonitrile

et al. 2019

View full text Add to dashboard Cite

show abstract

“…Interestingly,w ewerea ble to successfully grow crystalss uitable for SCXRD experiments (see the Supporting Information for details) of one of the representative examples,c ompound 1-4, to demonstrate the bent angle of the compound, which is an important parameteri nt he field of BCLCs and investigate the elusivec haracteristics of molecular packing (Figure 2a-f). [52][53][54][55][56][57] Compound 1-4 was found to crystallize in the monoclinic Figure 1. Chiral bent-core molecules with a) a ÀCH 3 moiety at the kink position (previously reported in ref.…”

Section: Single-crystal X-ray Diffraction (Scxrd) Studiesmentioning

confidence: 99%

Chiral Bent‐Shaped Molecules Exhibiting Unusually Wide Range of Blue Liquid‐Crystalline Phases and Multistimuli‐Responsive Behavior

Punjani

Mohiuddin

Kaur

et al. 2020

Chemistry A European J

View full text Add to dashboard Cite

Recently,a nu nprecedented observation of polar order,t hermochromic behavior,a nd exotic mesophases in new chiral, bent-shapeds ystemsw ith a ÀCH 3 moiety placed at the transverse position of the central core was reported. Herein,ah omologous series of compounds with even-numbered carbonc hains from n = 4t o1 8w ere synthesized, in which ÀCl was substituted for ÀCH 3 at the kink position and ad rastic modification in the phase structure of the bentshaped moleculew as observed. An unusuals tabilization of the cubic blue phase (BP) over aw ide range of 16.4 8Ch as been witnessed. Twoh omologues in this series (1-12 and 1-14) exhibit an interesting phase sequence consisting of BPI/ II, chiraln ematic, twist grain boundary,s mectic A, and smectic X( SmX) phases.T he higher homologues( 1-16 and 1-18) stabilizet he SmX phase enantiotropically over the entire temperature range. Crystal structure analysis confirmed the bent molecular architecture, with ab ent angle of 1488,a nd revealed the presenceo ft wo different molecular conformations in an asymmetric unit of compound 1-4. AD FT study corroborated that the ÀCl moiety at the central core of the molecule led to an increasei nt he dipole momenta long the transverse direction, which, in turn, facilitated the unusual stabilization of frustrated structures.C rystal polymorphism has been evidenced in three homologues( 1-10, 1-12, and 1-14) of the series. On the application of mechanical pressure through grinding, compound 1-10 transformedf rom a brighty ellow crystalline solid to ad ark orange-green amorphouss olid, which reversed upon dropwise additiono fd ichloromethane, indicating reversible mechanochromism in this class of compounds. In addition,e xcellent thermochromic behavior has been observed for compound 1-10w ith a controlled temperature-colorcombination.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.[a] Cr = crystal;I so = isotropic;N cyb * = chiral nematic phase composed of Sm clusters;T GBA = twist grain boundary phase;S mectic A = SmA; Smectic X = SmX. [b] Phaset ransitionso bserved by meanso fP OM in an ITO-coated planar cell (antiparallelrubbing). [c] Phase transitionso bserved by means of SAXS/WAXS.( 1-14: Cr 1a = amorphous,C r 2b = transition crystalline state, Cr 3c = crystal polymorph.)Chem.E ur.

show abstract

“…Carli et al 38 prepared a series of hydrogen bonded liquid crystalline supramolecular copolymers. They synthesized the tetra(ethyleneglycxoy)bis-4-benzoic acid (86) by referring to the literature report by Greuel et al; 39 later, it was mixed with the proton acceptors 1,2-bis(4-pyridyl)ethene (88) and 1,2-bis(4pyridyl)ethane (87) and converted to a molten state for two minutes in nitrogen atmosphere, followed by cooling the mixtures to room temperature to yield the expected complexes. Fig.…”

Section: Pyridine-based Molecules As Thermotropic Mesogensmentioning

confidence: 99%

“…An interesting fact is that these target compounds are emitters of blue uorescence in both the liquid crystalline state and solution state; hence, these compounds are potential candidates for OLED applications. Further, Ahipa et al 87 designed and synthesized compounds with a bent core structure with three rings, i.e. 4-(2-(4alkoxyphenyl)-6-methoxypyridin-4-yl)benzonitriles (208a-f), with variable alkoxy chain lengths.…”

Section: Pyridine-based Discotic Mesogensmentioning

confidence: 99%

Recent synthetic advances in pyridine-based thermotropic mesogens

Devadiga

Ahipa

2019

RSC Adv.

Self Cite

View full text Add to dashboard Cite

show abstract

New 4-(2-(4-alkoxyphenyl)-6-methoxypyridin-4-yl)benzonitriles: synthesis, liquid crystalline behavior and photo physical properties

Abstract: A new series of luminescent 4-(2-(4-alkoxyphenyl)-6-methoxypyridin-4-yl)benzonitriles containing three ring systems, with bent-core structures was synthesized as potential mesogens and characterized by spectral techniques.

Cited by 20 publications

References 41 publications

Hirshfeld Surface, Molecular Docking Study, Spectroscopic Characterization and NLO Profile of 2‐Methoxy‐4,6‐Diphenylnicotinonitrile

Hirshfeld Surface, Molecular Docking Study, Spectroscopic Characterization and NLO Profile of 2‐Methoxy‐4,6‐Diphenylnicotinonitrile

Chiral Bent‐Shaped Molecules Exhibiting Unusually Wide Range of Blue Liquid‐Crystalline Phases and Multistimuli‐Responsive Behavior

Recent synthetic advances in pyridine-based thermotropic mesogens

Contact Info

Product

Resources

About