Synthesis and mesomorphic properties of novel Schiff base liquid crystalline EDOT derivatives

Gowda, Ashwathanarayana; Roy, Arun; Kumar, Sandeep

doi:10.1016/j.molliq.2016.11.010

Cited by 27 publications

(6 citation statements)

References 39 publications

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“…Recently, we reported that a polymethacrylate with 4-methoxy- N -benzylideneaniline (MNBA) side groups (Figure a) shows a thermally stimulated photoinduced molecular reorientation based on axis-selective trans–cis–trans photoisomerization of the MNBA moieties using LP ultraviolet (UV) light exposure. , This behavior is similar to that of azobenzene-containing polymeric films. Because an aromatic imine (CN) bond is easily formed from aromatic aldehyde and amine derivatives, − coating 4-methoxyaniline (AN) molecules to form position-selective MNBA in a polymethacrylate film with phenyl aldehyde (PA) side groups leads to a photoinduced birefringent pattern . Additionally, an LC copolymethacrylate with benzoic acid (BA) and PA side groups ( P1 , Figure b) doped with AN in situ forms MNBA side groups, demonstrating cooperative thermally stimulated photoinduced molecular reorientation of the BA and MNBA side groups .…”

Section: Introductionmentioning

confidence: 99%

Photoinduced Reorientation and Photofunctional Control of Liquid Crystalline Copolymers with in Situ-Formed N-Benzylideneaniline Derivative Side Groups

et al. 2020

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The influence of the annealing conditions on the thermally stimulated photoinduced molecular reorientation of a photoinactive liquid crystalline polymethacrylate with phenyl aldehyde and benzoic acid side groups (P1) doped with 4-methoxyaniline, which forms photoalignable 4-methoxy-N-benzylideneaniline (MNBA) side groups in situ, was investigated. Light exposure and subsequent thermal stimulation under a N2 atmosphere realized sufficient cooperative molecular reorientation (D > 0.7), but the simultaneous thermal hydrolysis of the MNBA groups under humid air lowered the molecular reorientation performance. By contrast, subsequent thermal hydrolysis of MNBA after molecular reorientation introduced different aromatic amines into the reoriented P1 film, which regulated the birefringence and photofunctionality of the oriented film.

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Section: Introductionmentioning

confidence: 99%

Photoinduced Reorientation and Photofunctional Control of Liquid Crystalline Copolymers with in Situ-Formed N-Benzylideneaniline Derivative Side Groups

et al. 2020

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“…So, it is possible to assume that effective and safe small molecules can be developed to inhibit JNK1. Schiff bases, which are small molecules, and their complexes have certain properties such as chemo sensor [20,21], catalytic [22], optical switching devices [23], solvato chromic [24,25], fluorescent material [24], and liquid crystal [26]. Compounds derived from aromatic ortho hydroxy Schiff bases are of particular interest due to their nonlinear optical properties and abilities for polymerization and metal bond formation.…”

Section: Introductionmentioning

confidence: 99%

“…Compounds derived from aromatic ortho hydroxy Schiff bases are of particular interest due to their nonlinear optical properties and abilities for polymerization and metal bond formation. Moreover, various activity studies such as antifungal, antimicrobial, antimalarial, trypanocidal, antiproliferative, anti-inflammatory, antipyretic, herbicide and antitumor activity such compounds are available in the literature [20,21,33,34,22,[26][27][28][29][30][31][32].…”

Section: Introductionmentioning

confidence: 99%

Potansiyel JNK1 İnhibe Edici Aktiviteye Sahip 2-((4-(dimetilamino)benziliden)amino)-5-metilfenol’ün Sentezi, Teorik Çalışmaları, Sitotoksisitesi

Karaosmanoğlu

Berber

Uysal

2023

Süleyman Demirel Üniversitesi Sağlık Bilimleri Dergisi

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Cisplatin, doxorubicin, hydroxycamptothecin, leucovorin, vincristine and 5-fluorouracil resistance of cancer cells are associated with the activities of C-Jun N-Terminal Kinase 1 (JNK1). Inhibition of the JNK1 by pharmacological agents could be a beneficial attempt for reversing the chemoresistance of various cancer cells. However, there is no FDA-approved JNK inhibitor for safe use in clinics in today’s clinics. In this study, a Schiff base 2-((4-(dimethylamino)benzylidene)amino)-5-methylphenol, (7S4) has been synthesized and characterized by 1H, 13C-NMR, FT-IR and elemental analysis. The stable geometry of 7S4 has been determined by DFT method with Gaussian09 program (B3LYP/6-311g++(d,p))). The Gibbs Free energies, stable tautomer forms, H-bond, Mulliken charges, dipole moment, natural bond orbital (NBO), HOMO, LUMO and band gap energy (EGAP), molecular electrostatic potential (MEP) and solvent accessibility surface areas (SASA) have been calculated. Drug-likeness, anticancer and JNK1 inhibitory activities of 7S4 have been evaluated. Enol tautomer form of trans 7S4 was characterized as the most stable structure. 7S4 was observed to be a reactive compound in chemical reactions with a low EGAP value. In addition, high and low electron density regions of 7S4 are responsible for the establishment of chemical bonds in biological systems. 7S4 exhibited strong druggability with the agreement on Lipinski, Ghose, Veber, Egan, and Muegge rules. Cytotoxicity tests and molecular docking revealed that 7S4 poses a potential JNK1 inhibitor activity.

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“…Bu küçük moleküllerin moleküller arası etkileşimlerini arttırmak için çeşitli heteroatomların bağlanmasıyla elektron delokalizasyonu ve yüksek yük taşıma kapasitesi kolaylıkla arttırılabilir. Literatürde Schiff bazları ve komplekslerinin kemosensör [5], katalitik [6], solvatokromik [7], boyar madde [8] olarak kullanımlarına ve sıvı kristal özellikleri [9] nedeniyle de birçok alanda kullanımlarına yönelik çalışmalar mevcuttur. Ayrıca Schiff bazları biyolojik aktivite çalışmalarında da kullanılmaktadır [10][11][12].…”

Section: Introductionunclassified

2-((2-Hidroksibenziliden)amino)-4-Nitrofenol Schiff Bazının Teorik Olarak İncelenmesi ve Bazı Quantum Kimyasal Parametrelerinin Hesaplanması

Berber

UYSAL

2021

Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi

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Özet: 2-((2-Hidroksibenziliden)amino)-4-nitrofenol Schiff bazı bileşiğinin konformasyon analizi; DFT yönteminde, B3LYP metodu ve 6-311G++(d,p) temel seti ile yapılmış ve bileşiğin cis ve trans izomerlerinin konformasyonları teorik olarak hesaplanarak en kararlı konformasyonlar belirlenmiştir. Toplam enerjileri ve dihedral açıları hesaplanarak keto ve enol formlarının tautomer kararlılıkları belirlenmiştir. Enol tautomer formundaki molekülün keto tautomer formuna dönmesi sürecindeki enerji değişimleri yorumlanmıştır. Bileşiğin kararlı konformasyonu ile IR, 1 H ve 13 C NMR, UV-Vis., dipol moment, H-bağları, atomik yükleri (NBO), HOMO, LUMO ve bant aralığı enerjileri (EGAP), moleküler elektrostatik potansiyel şekli (MEP) ve çözücü erişilebilir yüzey alanı (SASA) hesaplamaları yapılmıştır. Molekülün optik ve metalik iletkenlik gibi elektronik özelliklere sahip aday molekül olduğu düşünülmektedir. SASA şeklinden molekülün polar ve polar protik çözücülerle güçlü etkileşim merkezlerinin olduğu ve biyolojik sistemler için de aktif merkezler içerdiği düşünülmektedir.

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Synthesis and mesomorphic properties of novel Schiff base liquid crystalline EDOT derivatives

Cited by 27 publications

References 39 publications

Photoinduced Reorientation and Photofunctional Control of Liquid Crystalline Copolymers with in Situ-Formed N-Benzylideneaniline Derivative Side Groups

Photoinduced Reorientation and Photofunctional Control of Liquid Crystalline Copolymers with in Situ-Formed N-Benzylideneaniline Derivative Side Groups

Potansiyel JNK1 İnhibe Edici Aktiviteye Sahip 2-((4-(dimetilamino)benziliden)amino)-5-metilfenol’ün Sentezi, Teorik Çalışmaları, Sitotoksisitesi

2-((2-Hidroksibenziliden)amino)-4-Nitrofenol Schiff Bazının Teorik Olarak İncelenmesi ve Bazı Quantum Kimyasal Parametrelerinin Hesaplanması

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