Synthesis and second order nonlinear optical properties of new chromophores containing 1,3,4-oxadiazole and thiophene rings

Carella, Antonio; Castaldo, Anna; Centore, Roberto; Fort, Alain; Sirigu, Augusto; Tuzi, Angela

doi:10.1039/b207230k

Cited by 45 publications

(33 citation statements)

References 18 publications

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“…Recently, it has been proved that the introduction of aromatic heterocyclic rings along the conjugation path results in increased hyperpolarizability in comparison with all benzenoid systems. [9][10][11] This is due to the delocalization energy of heteroaromatics, which is lower than that of six-membered rings. Chromophores containing aromatic pentaatomic heterocycles or their derivatives, such as thiophene, [12][13][14] thiazole, 15,16 benzothiazole, 16,17 and benzoxazole, 18,19 are among the most studied systems.…”

Section: Introductionmentioning

confidence: 96%

Development of polyurethanes with azo‐type chromophores for second‐order nonlinear optical applications

Tambe

Tasaganva

Jogul³

et al. 2009

J of Applied Polymer Sci

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Active nonlinear optical nitro-substituted thiazole, benzothiazole, and thiadiazole chromophores were prepared and condensed with tolylene-2,4-diisocyanate (TDI) and 4,4 0 -methylenedi(phenyl isocyanate) (MDI) to yield a series of polyurethanes. The resulting polyurethanes were characterized with Fourier transform infrared, proton nuclear magnetic resonance, and ultraviolet-visible spectroscopy, differential scanning calorimetry, thermogravimetric analysis, and gel permeation chromatography. The weight-average molecular weights of the polyurethanes ranged between 19,500 and 28,000 (weight-average molecular weight/number-average molecular weight ¼ 1.71-2.15). All the polyurethanes exhibited excellent solubility in most common organic solvents, and this indicated that these polyurethanes offered good processability. The glass-transition temperatures (T g 's) of the polyurethanes were in the range of C. Among the polyurethanes, chromophores containing the nitrothiazole moiety exhibited lower T g values in comparison with those of chromophores containing nitrobenzothiazole and nitrothiadiazole moieties. This was attributed to the small size of the nitrothiazole moiety in the polyurethane matrix. The polyurethanes containing a TDI backbone demonstrated relatively high T g values in comparison with those of the polyurethanes containing an MDI backbone. This was a result of an enhancement of the rigidity caused by the incorporation of a toluene ring into the polyurethane backbone. The second harmonic generation (SHG) coefficients of the poled polyurethane films ranged from 67.29 to 105.45 pm/V at 1064 nm. High thermal endurance of the poled dipoles was observed for all the polyurethanes. This was attributed to the formation of extensive hydrogen bonds between urethane linkages. Furthermore, none of the developed polyurethanes showed SHG decay below 150 C, and this signified their acceptability for nonlinear optical devices.

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Section: Introductionmentioning

confidence: 96%

Development of polyurethanes with azo‐type chromophores for second‐order nonlinear optical applications

Tambe

Tasaganva

Jogul³

et al. 2009

J of Applied Polymer Sci

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“…Generally, an increase in the β value is accompanied by a bathochromic shift due to a larger π-conjugated length and/or stronger donor and acceptor ability [9][10][11][12][13]. Therefore, there is always a tradeoff between nonlinearity and transparency [14][15][16][17][18][19][20][21][22][23]. To resolve this problem, we had designed and synthesized a series of H-typed chromophores with two parallel and nonconjugated D-π-A units [24][25][26][27].…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study of Effect of the Number of N,N-dimethyl-4-nitroaniline Units in Novel “Parallel Connection” Chromophores on Its Nonlinear Optical Properties

Zhang

Cao

Zhaobing

2012

ISRN Physical Chemistry

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Design of "parallel connection" chromophores could give a way of acquiring effective chromophores. The semiempirical method ZINDO was employed to study relationship between static first hyperpolarizabilities of "parallel connection" chromophores and the number of parallel nonconjugated N,N-dimethyl-4-nitroaniline (DMNA) units in the chromophore. The results show that the chromophore containing three parallel non-conjugated DMNA units exhibits the highest static first hyperpolarizability, which is 1.8 times that of chromophore DMNA. However, static first hyperpolarizabilities of the chromophores containing four or five DMNA units are very small. The absorption maximum wavelength (λ max ) of "parallel connection" chromophores is remarkably shorter (34.9 nm-38.1 nm) than that of 1DMNA. Therefore, the "parallel connection" chromophore containing three DMNA units would be an effective chromophore with a large first hyperpolarizability and a good optical transparency. It could give a useful suggestion for designing effective chromophores containing parallel non-conjugated D-π-A units.

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“…Poled organic thin films are technologically useful materials [1][2][3][4][5][6][7][8][9] which have several advantages over traditional inorganic crystals including ease of processing [10], larger second order susceptibilities [11], an intrinsically low dielectric constant [10], and significantly faster responses [12][13][14][15]. Our approach to poled organic films involves surfaceinduced polar alignment of main chain noncentrosymmetric hydrogen bonded liquid crystalline macromolecules [16].…”

Section: Introductionmentioning

confidence: 99%

Main Chain Noncentrosymmetric Hydrogen Bonded Macromolecules Incorporating Aniline, Alkanol, and Alkanoic Acid Hydrogen Bond Donors

Wolf

2014

Journal of Polymers

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The syntheses and characterization of three noncentrosymmetric main chain hydrogen bonded macromolecules which incorporate aniline, alkanoic acid, and alkanol hydrogen bond donor units are reported. These macromolecules participate in weak intermolecular hydrogen bonding as demonstrated using attenuated total reflectance (ATR) FTIR. The phase transitions of these macromolecules depend on the identity of the hydrogen bond donor.

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Synthesis and second order nonlinear optical properties of new chromophores containing 1,3,4-oxadiazole and thiophene rings

Cited by 45 publications

References 18 publications

Development of polyurethanes with azo‐type chromophores for second‐order nonlinear optical applications

Development of polyurethanes with azo‐type chromophores for second‐order nonlinear optical applications

Theoretical Study of Effect of the Number of N,N-dimethyl-4-nitroaniline Units in Novel “Parallel Connection” Chromophores on Its Nonlinear Optical Properties

Main Chain Noncentrosymmetric Hydrogen Bonded Macromolecules Incorporating Aniline, Alkanol, and Alkanoic Acid Hydrogen Bond Donors

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