N-Arylation of Protected and Unprotected 5-Bromo 2-Aminobenzimidazole as Organic Material: Non-Linear Optical (NLO) Properties and Structural Feature Determination through Computational Approach

The interest in the NLO response of organic compounds is growing rapidly, due to the ease of synthesis, availability, and low loss. Here, in this study, Cu(II)-catalyzed selective N-arylation of 2-aminobenzoimidazoles derivatives were achieved in the presence of different bases Et3N/TMEDA, solvents DCM/MeOH/H2O, and various aryl boronic acids under open atmospheric conditions. Two different copper-catalyzed pathways were selected for N-arylation in the presence of active nucleophilic sites, providing a unique tool for the preparation of NLO materials, C-NH (aryl) derivatives of 2-aminobenzoimidazoles with protection and without protection of NH2 group. In addition to NMR analysis, all synthesized derivatives (1a–1f and 2a–2f) of 5-bromo 2-amino benzimidazole (1) were computed for their non-linear optical (NLO) properties and reactivity descriptor parameters. Frontier molecular orbital (FMO) analysis was performed to get information about the electronic properties and reactivity of synthesized compounds.

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Tuning Second-Order Non-linear (NLO) Optical Response of Organoimido-Substituted Hexamolybdates through Halogens: Quantum Design of Novel Organic-Inorganic Hybrid NLO Materials

Australian Journal of Chemistry ◽

10.1071/ch10094 ◽

2010 ◽

Vol 63 (5) ◽

pp. 836 ◽

Cited By ~ 23

Author(s):

Muhammad Ramzan Saeed Ashraf Janjua ◽

Zhong-Min Su ◽

Wei Guan ◽

Chun-Guang Liu ◽

Li-Kai Yan ◽

...

Keyword(s):

Charge Transfer ◽

Phenyl Ring ◽

Density Functional ◽

Organic Ligand ◽

Second Order ◽

Inorganic Hybrid ◽

Nlo Properties ◽

Nlo Response ◽

Non Linear ◽

Nlo Materials

The second-order non-linear optical (NLO) response of organoimido-substituted hexamolybdates has been tuned from 218.61 × 10–30 to 490.10 × 10–30 esu. The dipole polarizabilities and second-order nonlinear optical (NLO) properties of organoimido derivatives of hexamolybdates have been investigated by using the time-dependent density functional response theory (TDDFT). The electron withdrawing ability of F (fluorine) has played an important role in tuning the second-order NLO response in this class of organic-inorganic hybrid compounds; particularly system 6 [Mo6O18(NC16H8F2(CF3)2I)]2– with the static second-order polarizability (βvec ) computed to be 490.10 × 10–30 esu. Thus, our studied systems have the feasibility to be excellent tuneable second-order NLO materials. The analysis of the major contributions to the βvec value suggests that the charge transfer (CT) from POM to organic ligand (D-A) along the z-axis has been enhanced with addition of F atoms at the end phenyl ring which directs head (POM) to tail (fluorinated ring) charge transfer. The computed βvec values have been tuned by incorporation of different halogen atoms at the end phenyl ring of organoimido segment. Furthermore, substitution of two trifluoromethyl (–CF3) groups sideways along with iodine (I) at the terminus of end phenyl ring in the organoimido ligand has a striking influence on tuning the optical non-linearity, as CT from POM to the organoimido ligand was significantly increased. These systematic small changes in molecular composition by substitution of different halogen groups leads to a tuning the NLO response; the so-called ‘ripple effect’ catches this point nicely. Thus, the present investigation provides thought provoking insight into the tuneable NLO properties of organoimido-substituted hexamolybdates.

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Chromophores with side isolate groups and applications in improving the poling efficiency of second non-linear optical (NLO) materials

Dyes and Pigments ◽

10.1016/j.dyepig.2018.11.001 ◽

2019 ◽

Vol 162 ◽

pp. 721-727 ◽

Cited By ~ 1

Author(s):

Qiuli Cheng ◽

Xiaoyu Shi ◽

Chuangyang Li ◽

Yuhang Jiang ◽

Zuosen Shi ◽

...

Keyword(s):

Non Linear ◽

Nlo Materials ◽

Linear Optical

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First Principle Study of Electronic and Non-Linear Optical (NLO) Properties of Triphenylamine Dyes: Interactive Design Computation of New NLO Compounds

Australian Journal of Chemistry ◽

10.1071/ch15402 ◽

2016 ◽

Vol 69 (4) ◽

pp. 467 ◽

Cited By ~ 9

Author(s):

Muhammad Ramzan Saeed Ashraf Janjua ◽

Zain Hassan Yamani ◽

Saba Jamil ◽

Asif Mahmood ◽

Imran Ahmad ◽

...

Keyword(s):

Density Functional Theory ◽

Absorption Spectra ◽

Density Functional ◽

Conjugation Length ◽

Functional Theory ◽

Nlo Properties ◽

Non Linear ◽

Design Computation ◽

Notable Increase ◽

Linear Optical

In this study, density functional theory and time-dependent density functional theory are used to determine how the size of π-conjugated system influences the absorption spectra and non-linear optical (NLO) properties of dyes. Double and triple bonds, as well the benzene rings, are used in conjugated systems. The results of the theoretical computation show that the absorption spectra are gradually broadened and red-shifted with increases in the conjugation length. Theoretical examination of the NLO properties was performed on the key parameters of polarizability and hyperpolarizability. A notable increase in the non-linear optical response was observed with an increase in the conjugation length of the π-spacer.

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Wavelength dependent nonlinear optical response of tetraphenylethene aggregation-induced emission luminogens

Materials Chemistry Frontiers ◽

10.1039/c8qm00375k ◽

2018 ◽

Vol 2 (12) ◽

pp. 2263-2271 ◽

Cited By ~ 15

Author(s):

Jianbo Xiong ◽

Xinyue Li ◽

Chunqing Yuan ◽

Sergey Semin ◽

Zhaoquan Yao ◽

...

Keyword(s):

Optical Properties ◽

Nonlinear Optical ◽

Theoretical Calculations ◽

Experimental Results ◽

Nlo Properties ◽

Aggregation Induced Emission ◽

Non Linear ◽

Potential Applications ◽

Linear Optical Properties ◽

Linear Optical

Studies of the non-linear optical properties of classical AIEgens are rare, despite their important potential applications in organic composite photonic circuits. Here, we present experimental results, supported by theoretical calculations, of the non-linear optical (NLO) properties of TPE and its halogenated derivates.

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Synthesis, linear & non linear optical (NLO) properties of some indoline based chromophores

Dyes and Pigments ◽

10.1016/j.dyepig.2010.10.010 ◽

2011 ◽

Vol 89 (2) ◽

pp. 177-187 ◽

Cited By ~ 28

Author(s):

M. Delower H. Bhuiyan ◽

Mohamed Ashraf ◽

Ayele Teshome ◽

Graeme J. Gainsford ◽

Andrew J. Kay ◽

...

Keyword(s):

Nlo Properties ◽

Non Linear ◽

Linear Optical

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Synthesis and non-linear optical characterization of novel borinate derivatives of cinnamaldehyde

New Journal of Chemistry ◽

10.1039/b820435g ◽

2009 ◽

Vol 33 (8) ◽

pp. 1693 ◽

Cited By ~ 21

Author(s):

Mario Rodríguez ◽

José Luis Maldonado ◽

Gabriel Ramos-Ortíz ◽

Jean François Lamère ◽

Pascal G. Lacroix ◽

...

Keyword(s):

Optical Characterization ◽

Non Linear ◽

Linear Optical ◽

Derivatives Of

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Spectral and non-linear optical properties of cyanine bases' derivatives of benzo[c,d]indole

Dyes and Pigments ◽

10.1016/j.dyepig.2006.01.048 ◽

2007 ◽

Vol 74 (1) ◽

pp. 195-201 ◽

Cited By ~ 12

Author(s):

O TOLMACHEV ◽

N PILIPCHUK ◽

O KACHKOVSKY ◽

Y SLOMINSKI ◽

V GAYVORONSKY ◽

...

Keyword(s):

Optical Properties ◽

Non Linear ◽

Linear Optical Properties ◽

Linear Optical ◽

Derivatives Of

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Synthesis, crystal structure and non-linear optical properties of boronates derivatives of salicylideniminophenols

Journal of Organometallic Chemistry ◽

10.1016/j.jorganchem.2008.01.032 ◽

2008 ◽

Vol 693 (7) ◽

pp. 1321-1334 ◽

Cited By ~ 28

Author(s):

Blanca M. Muñoz ◽

Rosa Santillan ◽

Mario Rodríguez ◽

José Manuel Méndez ◽

Margarita Romero ◽

...

Keyword(s):

Crystal Structure ◽

Optical Properties ◽

Non Linear ◽

Linear Optical Properties ◽

Linear Optical ◽

Derivatives Of

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[A3X][Ga3PS8] (A = K, Rb; X = Cl, Br): promising IR non-linear optical materials exhibiting concurrently strong second-harmonic generation and high laser induced damage thresholds

Chemical Science ◽

10.1039/c6sc01907b ◽

2016 ◽

Vol 7 (9) ◽

pp. 6273-6277 ◽

Cited By ~ 86

Author(s):

Bin-Wen Liu ◽

Hui-Yi Zeng ◽

Xiao-Ming Jiang ◽

Guan-E Wang ◽

Shu-Fang Li ◽

...

Keyword(s):

Second Harmonic Generation ◽

Harmonic Generation ◽

Optical Materials ◽

Second Harmonic ◽

High Laser ◽

Non Linear ◽

Nlo Materials ◽

Linear Optical ◽

Laser Induced Damage

We have developed a new series of salt-inclusion chalcogenides, which are promising IR-NLO materials exhibiting large second-harmonic generation and high laser-induced damage thresholds.

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