Dramatically enhanced second-order nonlinear optical susceptibilities in tricyanovinylthiophene derivatives

Rao, V. Pushkara; Jen, Alex K.‐Y.; Wong, Kwan-Yee K.; Drost, Kevin J.

doi:10.1039/c39930001118

Cited by 148 publications

(57 citation statements)

References 9 publications

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“…The design strategy, used by many with success involves connecting donor (D) and acceptor (A) groups at the terminal positions of a p-bridge to create highly polarized molecules that could exhibit large molecular nonlinearity [3]. Till date, the types of p-bridges investigated for developing efficient NLO materials and molecules include D-A olefines [4,5], acetylenes [6], azo bridges [7], aromatic [8] and heteroaromatic rings [9,10].…”

Section: Introductionmentioning

confidence: 99%

Linear and non-linear optical properties of some donor–acceptor oxadiazoles by ab initio Hartree-Fock calculations

2008

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The molecular hyperpolarizability of some donor-acceptor oxadiazoles was investigated using ab initio methods. Ab initio optimizations were performed at the Hartree-Fock level using different basis sets, starting with the minimal basis set, and then split valence sets. The first hyperpolarizabilities were calculated at the Hartree-Fock level employing the corresponding basis sets using Gaussian 98W. In general, the first hyperpolarizability is dependent on the choice of method and basis set. In order to understand this phenomenon in the context of molecular orbital picture, we examined the molecular HOMOs and molecular LUMOs generated via HF/6-31G level. It has also been calculated the polarizability, anisotropy of polarizability and ground state dipole moment of all the molecules. Several of these oxadiazoles display significant second-order molecular nonlinearity, b(8.57-195.05 9 10 -30 esu) and provide the basis for future design of efficient nonlinear optical materials having the oxadiazole core.

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Section: Introductionmentioning

confidence: 99%

Linear and non-linear optical properties of some donor–acceptor oxadiazoles by ab initio Hartree-Fock calculations

2008

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“…45 The influence of the substituent on the nitrogen atom of the pyrrole ring is demonstrated by comparison of the absorption maxima of compounds 1a 1 and 1e as the longest wavelength transition is shifted from 491.5 nm in 1-(n-propyl)-2-(2´-thienyl)-5-tricyanovinylpyrrole 1a 1 ( Table 1, It is widely recognized that low energy bands in the UV-vis. spectra 46 and large solvatochromism 7,[47][48] are good indicators of potential NLO properties.…”

Section: Uv-visible Study Of Tricyanovinyl-substituted Thienylpyrrolesmentioning

confidence: 99%

Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties

et al. 2005

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-Tricyanovinyl-substituted 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 1 have been synthesized by direct tricyanovinylation reaction of 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 2 using TCNE. The tricyanovinyl-derivatives 1 display dramatic reductions in both their optical and electrochemical band gaps relative to thienylpyrrole precursors 2. The solvatochromic behavior of compounds 1 was investigated in a variety of solvents. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities β of the mentioned compounds. The β values show that the new compounds prepared could be used on the manufacture of materials with good non-linear (NLO) properties.

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“…Another observed issue is that the incorporation of benzene rings into the aliphatic push-pull polyenes results in saturation of the molecular nonlinearity (Varanasi et al 1996). To overcome this problem, several groups (Rao et al 1993(Rao et al , 1994Varanasi et al 1996) have developed NLO chromophores containing easily polarizable five membered heteroaromatic rings. Heterorings such as furan and thiophene, due to their relatively lower aromatic stabilization energy than benzene, are reported to provide more effective p-conjugation between D and A, resulting in larger nonlinearities (Varanasi et al 1996).…”

Section: Introductionmentioning

confidence: 99%

“…To date, the types of p-bridges investigated for developing efficient NLO materials and molecules include D-A olefines (Marder et al 1994;Blanchard-Desce et al 1995), acetylenes (Cheng et al 1991a), azo bridges (Moylan et al 1993), and aromatic (Cheng et al 1991b;Ruanwas et al 2010) and heteroaromatic rings (Rao et al 1993(Rao et al , 1994. Although push-pull polyenes generally show a large first hyperpolarizability, their thermal stability is not satisfactory.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and nonlinear optical characterization of new 1,3,4-oxadiazoles

et al. 2011

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A new series of 1,3,4-oxadiazole derivatives containing 2-fluoro-4-methoxy phenyl were synthesized by refluxing mixture of acid hydrazide 3 with different aromatic carboxylic acids (a-e) in phosphorous oxychloride. These newly synthesized compounds were characterized by NMR, mass spectral, and IR spectral studies, and also by C, H, N analyses. The open-aperture z-scan experiment was employed to measure the optical nonlinearity of the samples at 532 nm, using 5 ns laser pulses. The measurements indicate that compound 4a, which contains Bromine, behaves as an optical limiter at this wavelength, with potential applications in optoelectronics.

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Dramatically enhanced second-order nonlinear optical susceptibilities in tricyanovinylthiophene derivatives

Cited by 148 publications

References 9 publications

Linear and non-linear optical properties of some donor–acceptor oxadiazoles by ab initio Hartree-Fock calculations

Linear and non-linear optical properties of some donor–acceptor oxadiazoles by ab initio Hartree-Fock calculations

Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties

Synthesis and nonlinear optical characterization of new 1,3,4-oxadiazoles

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