Influence of inter- and intramolecular H-bonding on the mesomorphic and photoswitching behaviour of (E)-4-((4-(hexyloxy)phenyl)diazenyl)-N-phenyl benzamides

Sunil B. N.; Behera Paresh Kumar; Achalkumar Ammathnadu S.; Shanker G.; Hegde Gurumurthy

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Influence of inter- and intramolecular H-bonding on the mesomorphic and photoswitching behaviour of (E)-4-((4-(hexyloxy)phenyl)diazenyl)-N-phenyl benzamides

机译：（e）-4-（（4-（己氧基）苯基）二亚苯基）-N-苯基苯甲酰胺的间骨和分子分子H键对细胞和分子分子H键合的影响

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We report on the synthesis, phase behaviour and photoswitching studies of new azo linked rod-shaped molecules. These novel materials consist of three phenyl rings separated by a diazo, amide linkage with a hexyloxy tail and 2,4-substituents at either end of the phenyl ring. The mesomorphic behaviours, phase transition temperature including the enthalpies were characterized by polarizing optical microscope (POM) and differential scanning calorimetry (DSC). The influence of inter- and intramolecular hydrogen bonding on mesomorphic and photoisomerization was studied. Photoisomerization studies carried out both in the solid and liquid phase show the quick E-Z transition with prolonged thermal back relaxation (Z-E) by using UV-Visible spectroscopy. This interesting behaviour could be attributed to the presence of the hexyloxy tail, lateral electron withdrawing group and the influence of inter- or intramolecular hydrogen bonding. Excellent bright and dark states were accomplished using one of these materials in optical storage device. Further tuning is necessary to employ them for real applications.

机译：我们报道了新的偶氮连接棒状分子的合成，相行为和光学开养研究。这些新颖的材料由三个由二氮杂分开的三个苯环，与苯环的任一端的己氧基尾和2,4-取代基分开。通过偏振光学显微镜（POM）和差示扫描量热法（DSC），表征了包括焓的中间形行为，包括焓的相变温度。研究了研究和分子内氢键对中间形和光异构化的影响。在固体和液相中进行的光血机化研究表明，通过使用UV可见光光谱，通过延长热背部弛豫（Z-E）的快速E-Z过渡。这种有趣的行为可归因于存在己氧基尾，侧向电子抽出组和间氨基间氢键的影响。使用这些材料中的一种在光学存储装置中完成优异的明亮和暗状态。为使用它们进行进一步调整以实现实际应用。

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《RSC Advances》 |2020年第34期|共9页
作者
Sunil B. N.; Behera Paresh Kumar; Achalkumar Ammathnadu S.; Shanker G.; Hegde Gurumurthy;
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BMS Coll Engn Ctr Nanomat &

Displays BMS R&

D Ctr Bangalore 560019 Karnataka India;

Indian Inst Technol Guwahati Dept Chem Gauhati 781039 Assam India;

Indian Inst Technol Guwahati Dept Chem Gauhati 781039 Assam India;

Bangalore Univ Dept Chem Jnana Bharathi Campus Bangalore 560056 Karnataka India;

BMS Coll Engn Ctr Nanomat &

Displays BMS R&

D Ctr Bangalore 560019 Karnataka India;

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1. Influence of inter- and intramolecular H-bonding on the mesomorphic and photoswitching behaviour of (E)-4-((4-(hexyloxy)phenyl)diazenyl)-N-phenyl benzamides [J] . Sunil B. N., Behera Paresh Kumar, Achalkumar Ammathnadu S., RSC Advances . 2020,第34期

机译：（e）-4-（（4-（己氧基）苯基）二亚苯基）-N-苯基苯甲酰胺的间骨和分子分子H键对细胞和分子分子H键合的影响
2. X-ray powder diffraction data for N-[4-(aminocarbonyl)phenyl]-4-[2-[1-[[(2,3-dihydro-2-oxo-1H-benzimidazol-5-yl)amino]carbonyl]-2-oxopropyl]diazenyl]-benzamide, a p-form of pigment yellow 181 [J] . J. Maixner, R. Pazout, J. Cibulkova, Powder diffraction . 2011,第3期

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3. Influence of the ester chain length on the mesogenic behavior and optical anisotropy of 4-[[4-(butoxy) phenyl] diazenyl] phenyl alkanoates [J] . Niezgoda Izabela, Szypszak Ewelina, Dardas Dorota, Phase Transitions . 2016,第4期

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4. Synthesis, characterization and mesomorphic properties of N,N'-(1,,4-phenylene (methanylylidene))bis(4-(hexyloxy)aniline) [C] . Caldera Villalobos Martin, Garcia Serrano Jesus, Herrera Gonzalez Ana Maria National Congress of Science and Materials Engineering . 2014

机译：N，N' - （1，4-苯基（甲基丙烯））双（4-（己氧基）苯胺）的合成，表征和中晶特性
5. Synthesis and Acetylcholinesterase Inhibitory Evaluation of 4-(13-Dioxoisoindolin-2-yl)-N-Phenyl Benzamide Derivatives as Potential Anti-Alzheimer Agents [O] . Ahmad Mohammadi-Farani, Samira Soltani Darbandi, Alireza Aliabadi 2016

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6. Bis{μ-ethyl 4-[(4-hydroxyphenyl)diazenyl]benzoate-κO}bis[aqua(4-{[4-(ethoxycarbonyl)phenyl]diazenyl}phenolato-κO){ethyl 4-[(4-hydroxyphenyl)diazenyl]benzoate-κO}potassium] [O] . Felipi Ramiro Sobral, Juliano Rosa de Menezes Vicenti, Roberta Cargnelutti, 2017

机译：双{μ-乙基4 - [（4-羟基苯基）二氮烯基]苯甲酸-κO}双[aqua（4 - {[4-（乙氧基羰基）苯基]二氮烯基} phenolato-κO）{乙基4 - [（4-羟基苯基）二氮烯基]苯甲酸甲酯，κO}钾]

Influence of inter- and intramolecular H-bonding on the mesomorphic and photoswitching behaviour of (E)-4-((4-(hexyloxy)phenyl)diazenyl)-N-phenyl benzamides

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