Synthesis and characterization of thiazole-containing chromophores for second-order nonlinear optics

Wang, Yuh-Kai; Shu, Ching‐Fong; Breitung, Eric M.; McMahon, Robert J.

doi:10.1039/a900820i

Cited by 57 publications

(27 citation statements)

References 11 publications

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“…Thiophene is a very good auxiliary donor insofar as it is electron-rich and, at the same time, is highly aromatic (compared with, for example, pyrrole or furane, which show more 1,3-diene character). Indeed, chromophores with thiophene as part of the bridging p-conjugated system display enhanced first molecular hyperpolarizabilities compared with pyrrole [11,20] or benzene [9,[21][22][23] analogues.…”

Section: Introductionmentioning

confidence: 99%

“…In the design of a conjugated p-system between donor and acceptor moieties in push-pull molecules, the incorporation of aromatic five-membered heterocycles has received much attention and often results in enhanced first molecular hyperpolarizability [8][9][10][11][12][13][14][15][16][17][18]. However, a delicate interplay of various factors must be taken into account; on the one hand, the aromaticity of the heterocycle is obviously important in providing efficient electron transfer between donor and acceptor moieties whilst, in contrast, it is clear that the electronic nature of the heteroaromatic ring will determine whether it acts as an ''auxiliary donor'' or an ''auxiliary acceptor'' [19].…”

Section: Introductionmentioning

confidence: 99%

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Push–pull chromophores comprising benzothiazolium acceptor and thiophene auxiliary donor moieties: Synthesis, structure, linear and quadratic non-linear optical properties

et al. 2009

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a b s t r a c tNovel, push-pull chromophores combining a cationic benzothiazolium acceptor moiety and either one or two thiophene rings as a part of the conjugated p-system between the donor and the acceptor moieties have been synthesized and characterized. The chromophores displayed pronounced quadratic NLO activity with their first molecular hyper polarizabilities in agreement with their linear spectral properties.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Push–pull chromophores comprising benzothiazolium acceptor and thiophene auxiliary donor moieties: Synthesis, structure, linear and quadratic non-linear optical properties

et al. 2009

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“…A wide variety of structural modifications on the donoreacceptor and p-conjugated moieties have been carried out [3,4]. Major research efforts have focused on developing NLO chromospheres possessing large molecular nonlinearity and good thermal stability as well as improved solubility and process ability.…”

Section: Introductionmentioning

confidence: 99%

Novel dyes derived from hydrazones. Part 4. Synthesis and characterizations of 2-{4-[(2E)-2-(1-arylylidene)hydrazino]phenyl}ethylene-1,1,2-tricarbonitrile

Asiri¹,

Fatani²

2007

Dyes and Pigments

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Novel tricyanovinyl derived from hydrazones have been prepared by the reaction of tetracyanoethylene and phenylethylidene hydrazone, and these dyes showed absorption in the region of 500e593 nm. The dyes showed pronounced solvatochromic effects as the polarity of the solvents increased. Some of the new dyes were studied to show the aggregation properties in solution as the concentration changed. Most of the dyes studied showed change in the absorption spectrum and hence the position of the maximum absorption bands.The thermal stability of some of the prepared dyes was studied in polymethylmethacrylate film at 80 C; the annulations on the aromatic group showed less thermal stability of the dyes.

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“…Organic non-linear optics (NLO) materials formed by a donor-acceptor pair in their molecular system exhibit noteworthy NLO characteristics [7]. Thiazoles with a pushpull system containing electron-withdrawing and electron donating groups have been studied in the past years in order to develop derivatives to be used as NLO materials [7,8]. On the other hand, it is well known as an excellent ligand [9,10].…”

Section: Commentmentioning

confidence: 99%

Crystal structure of (E)-N,N-diethyl-2-(5-nitrothiazol-2-yl)-1-phenylethen-1-amine, C₁₅H₁₇N₃O₂S

Pairan

Kasim

Yamin

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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CCDC no.: 1558756The title crystal structure is shown in the figure. conditions. Table 2 lists the atoms with their coordinates and displacement parameters. Source of materialsThe title compound was synthesized from the Sonogashira Coupling-Aminovinylation Sequence reaction [4]. In a nitrogen atmosphere, a THF solution of phenylacetylene (1.1 mmol in 5 mL THF) was added dropwisely into a stirred mixture of 2-bromo-5-nitrothiazole (1 mmol), Pd(PPh 3 ) 2 Cl 2 (14 mg, 0.02 mmol), CuI (7 mg, 0.04 mmol), and 11 mL of THF/NEt 3 (10:1). The reaction mixture was stirred at room temperature overnight until conversion was complete (monitored by TLC). Then, a solution of diethylamine (2 mmol) in 5 mL of methanol was added, and the mixture was heated to reflux for ca. 9 hour until complete conversion (monitored by TLC). The solvents were evaporated in vacuo, and the residue was purified by chromatography over a short pad of aluminum oxide eluting with dichloromethane followed by acetone to yield 60% of the entitled compound. The residue was then recrystallized in dichloromethane by evaporation in vacuo, which yielded dark red crystals. After several attempts a suitable crystal for single X-ray diffraction study was obtained. Experimental detailsH atoms were fixed geometrically at ideal positions and allowed to ride on the parent atoms with C-H = 0.93-0.97 Å, with U iso (H) = 1.5Ueq(C) (for CH 3 )and 1.2 Ueq(C) (for CH 2 and CH).

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Synthesis and characterization of thiazole-containing chromophores for second-order nonlinear optics

Cited by 57 publications

References 11 publications

Push–pull chromophores comprising benzothiazolium acceptor and thiophene auxiliary donor moieties: Synthesis, structure, linear and quadratic non-linear optical properties

Push–pull chromophores comprising benzothiazolium acceptor and thiophene auxiliary donor moieties: Synthesis, structure, linear and quadratic non-linear optical properties

Novel dyes derived from hydrazones. Part 4. Synthesis and characterizations of 2-{4-[(2E)-2-(1-arylylidene)hydrazino]phenyl}ethylene-1,1,2-tricarbonitrile

Crystal structure of (E)-N,N-diethyl-2-(5-nitrothiazol-2-yl)-1-phenylethen-1-amine, C₁₅H₁₇N₃O₂S

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Synthesis and characterization of thiazole-containing chromophores for second-order nonlinear optics

Cited by 57 publications

References 11 publications

Push–pull chromophores comprising benzothiazolium acceptor and thiophene auxiliary donor moieties: Synthesis, structure, linear and quadratic non-linear optical properties

Push–pull chromophores comprising benzothiazolium acceptor and thiophene auxiliary donor moieties: Synthesis, structure, linear and quadratic non-linear optical properties

Novel dyes derived from hydrazones. Part 4. Synthesis and characterizations of 2-{4-[(2E)-2-(1-arylylidene)hydrazino]phenyl}ethylene-1,1,2-tricarbonitrile

Crystal structure of (E)-N,N-diethyl-2-(5-nitrothiazol-2-yl)-1-phenylethen-1-amine, C15H17N3O2S

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Crystal structure of (E)-N,N-diethyl-2-(5-nitrothiazol-2-yl)-1-phenylethen-1-amine, C₁₅H₁₇N₃O₂S