• 제목/요약/키워드: Oxadiazole

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Theroetical Study of the Nonlinear Optical Properties of Thiophene, Furan, Pyrrole, (1,2,4-triazole), (1,3,4-oxadiazole), and (1,3,4-thiadiazole) Monomers and Oligomers

  • 최우성;김태원;정승우;김철주
    • Bulletin of the Korean Chemical Society
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    • 제19권3호
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    • pp.299-307
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    • 1998
  • PM3 semiempirical calculations were carried out to study the frequency-dependent nonlinear optical properties of thiophene, furan, pyrrole, (1,2,4)-triazole, (1,3,4)-oxadiazole, and (1,3,4)-thiadiazole monomers and oligomers. The longitudinal component, αxx, is the largest of three principle components. On the other hand, the out-of-plane component, αzz, is the smallest. Moreover, the out-of-plane component (αzz) of thiophene, furan, pyrrole, (1,2,4)-triazole, (1,3,4)-oxadiazole, and (1,3,4)-thiadiazole monomers show constant changes with increasing optical frequencies. The frequency-dependent first- order polarizabilities increase in the order: thiophene > (1,2,4)-triazole > pyrrole > furan > (1,3,4)-thiadiazole > (1,3,4)-oxa-diazole monomers and oligomers. The effects of β(-2ω;ω,ω) (SHG) shows a larger dispersion compared with (-ω;ω,0) (EOPE) and β(0;-ω,ω) (OR). The second- order polarizabilities of thiophene, furan, pyrrole, (1,2,4)-triazole, (1,3,4)-thiadiazole, and (1,3,4)-oxadiazole monomers for the various second- order effects have the order: β(-2ω;ω,ω) (SHG) > β(-ω;ω,0) (EOPE) > β(0;-ω,ω) (OR) and thiophene > pyrrole > (1,2,4)-triazole > furan > 1,3,4-thiadiazole > 1,3,4-oxadiazole monomers. The third- order polarizabilities for the various third- order effects have the following order: γ(-3ω;ω',ω,ω) (THG) > γ(-2ω;0,ω,ω) (EFISHG) > γ(-ω;ω',-ω,ω) (IDRI) > γ(-ω;0,0,ω) (OKE). The effects of THG increase rapidly with increasing optical frequencies compared with the other effects. In particular, OKE effects increase most slowly with increasing optical frequencies. Also, the effects of THG for thiophene, furan, pyrrole, (1,2,4)-triazole, (1,3,4)-thiadiazole, and (1,3,4)-oxadiazole oligomers show the order thiophene > (1,2,4)-triazole > furan > pyrrole > (1,3,4)-thiadiazole > (1,3,4)-oxadiazole oligomers. In particular, the third- order polarizabilities of thiophene and (1,3,4)-thiadiazole oligomers are about four and three times larger than those of (1,3,4)-oxadiazole and (1,2,4)-triazole oligomer, respectively.

$\tau$-H$_2$PC/oxadiazole 유기이층막의 감광특성 연구 (I) (Electrophotographic properties of $\tau$-H$_2$Pc/oxadiazole photoreceptor (I))

  • 이덕출;박구범;조기선;오승현
    • 한국전기전자재료학회:학술대회논문집
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    • 한국전기전자재료학회 1993년도 추계학술대회 논문집
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    • pp.141-143
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    • 1993
  • A nontoxic organic photoreceptor for near infrared light has been developed. A double layered photoreceptor using $\tau$-H$_2$Pc as the CGL was made. The CTL was formed by oxadiazole derivative dispersed in two other host polymers. This photoreceptor has a charge acceptance of -900 V when a corona charge is used, and has residual potentials of -20 V for PC, and -10 V for PVB by light irradiation.

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Synthesis, PL and Electron drift mobility of new Diphenoquinones with conjugated oxadiazole (I)

  • Yang, Jong-Hyun;Ryu, Jung-Yi;Kang, Dong-Eun;Kim, Beom-Jun;Kim, Young-Soon;Chung, Su-Tae;Son, Se-Mo
    • 한국전기전자재료학회:학술대회논문집
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    • 한국전기전자재료학회 2002년도 하계학술대회 논문집 Vol.3 No.2
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    • pp.1006-1009
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    • 2002
  • A new phenoquinone with extended $\pi$-conjugate oxadiazole (DQEO) was synthesized. Absorption and photoluminescence of DQEO were appeared 330 nm. 420nm respectively. Electron drift mobility of DQEO were estimated by conventional time-of-flight (TOF) technique.

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Preparation of Fully Substituted 1,3,4-Oxadiazole Derivatives from N-Isocyaniminotriphenylphosphorane, (E)-Cinnamic Acids, Chloroacetone and Primary Amines

  • Ramazani, Ali;Nasrabadi, Fatemeh Zeinali;Karimi, Zahra;Rouhani, Morteza
    • Bulletin of the Korean Chemical Society
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    • 제32권8호
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    • pp.2700-2704
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    • 2011
  • The 1:1 imine intermediate generated by the addition of primary amine to chloroacetone is trapped by N-isocyaniminotriphenylphosphorane in the presence of (E)-cinnamic acids and the corresponding iminophosphorane intermediate was formed. Disubstituted 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were completed in neutral conditions at room temperature. The disubstituted 1,3,4-oxadiazole derivatives were produced in excellent yields.

Synthesis and Characterization of 1,2,4-Oxadiazole-Based Deep-Blue and Blue Color Emitting Polymers

  • Agneeswari, Rajalingam;Tamilavan, Vellaiappillai;Hyun, Myung Ho
    • Bulletin of the Korean Chemical Society
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    • 제35권2호
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    • pp.513-517
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    • 2014
  • Two donor-acceptor-donor monomers such as 3,5-bis(4-bromophenyl)-1,2,4-oxadiazole (BOB) and 3,5-bis(5-bromothiophen-2-yl)-1,2,4-oxadiazole (TOT) incorporating electron transporting and hole blocking 1,2,4-oxadiazloe moiety were copolymerized with light emitting fluorene derivative via Suzuki polycondensation to afford two new polymers, PFBOB and PFTOT, respectively. The optical studies for polymers PFBOB and PFTOT revealed that the band gaps are 3.10 eV and 2.72 eV, respectively, and polymer PFBOB exhibited a deep-blue emission while polymer PFTOT showed blue emission in chloroform and as thin film. The photoluminescence quantum efficiencies (${\Phi}_f$) of polymers PFBOB and PFTOT in chloroform calculated against highly blue emitting 9,10-diphenylanthracene (DPA, ${\Phi}_f=0.90$) were 1.00 and 0.44, respectively.

Microwave Assisted Synthesis of 1,3,4-Oxadiazole/Thiohydantoin Hybrid Derivatives via Dehydrative Cycliztion of Semicarbazide

  • Yang, Seung-Ju;Lee, Jae-Min;Lee, Gee-Hyung;Kim, NaYeon;Kim, Yong-Sang;Gong, Young-Dae
    • Bulletin of the Korean Chemical Society
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    • 제35권12호
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    • pp.3609-3617
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    • 2014
  • A series of compounds containing both 1,3,4-oxadiazole and thiohydantoin were synthesized as a promising scaffold for application in medicinal chemistry. The key step of the synthesis is a microwave-assisted cyclization of semicarbazides possessing a thiohydantoin moiety at one of the acyl termini using $POCl_3$ as a dehydrating reagent. A wide range of semicarbazides were prepared through the substitution of hydrazides with an N-acylated thiohydantoin derived from the cyclization of the corresponding isothiocyanate with an amino acid and subsequent N-acylation of the resultant thiohydrantion. Consequently, the 58 number of 1,3,4-oxadiazole derivatives having a thiohydantoin substituent were prepared in good overall yields.

One-pot, Three-component Synthesis of Fully Substituted 1,3,4-Oxadiazole Derivatives from (N-Isocyanoimino)triphenylphosphorane, Aromatic Carboxylic acids and (1R)-(-)-Campherchinon

  • Ramazani, Ali;Nasrabadi, Fatemeh Zeinali;Abdian, Behnaz;Rouhani, Morteza
    • Bulletin of the Korean Chemical Society
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    • 제33권2호
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    • pp.453-458
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    • 2012
  • Reactions of (N-isocyanimino)triphenylphosphorane with (1R)-(-)-campherchinon in the presence of aromatic carboxylic acids proceed smoothly at room temperature and in neutral conditions to afford sterically congested 1,3,4-oxadiazole derivatives in high yields. The reaction proceeds smoothly and cleanly under mild conditions and no side reactions were observed.

Synthesis and Characterization of Novel Oxadiazole Derivatives from Benzimidazole

  • Vishwanathan, Balasubramanaya;Gurupadayya, Bannimath
    • 대한화학회지
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    • 제58권5호
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    • pp.450-455
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    • 2014
  • In the present study, a series of novel N-(1H-benzo[d]imidazol-2-yl)methyl-5-[(hetero)aryl-1,3,4-oxadiazol-2-yl]methanamine (4a-4j) were efficiently synthesized. Condensation of hydrazide derivative 3 with various carboxylic acid derivatives yielded N-[(1H-benzo[d]imidazol-2-yl)methy](5-substituted-1,3,4-oxadiazol-2-yl)methanamine (4a-4j) and compound 5-{[(1H-benzo[d]imidazol-2-yl)methylamino]methyl}-1,3,4-oxadiazole-2-thiol (4k) was obtained on treating hydrazide 3 with carbon disulfide. All the newly synthesized analogues were characterized by IR, $^1H$ NMR, $^{13}C$ NMR and mass spectral data.

반응방법에 따른 1-Benzofuran-2-yl thiadiazoles, Triazoles과 Oxadiazoles의 합성 (Synthesis and Characterization of 1-Benzofuran-2-yl thiadiazoles, Triazoles and Oxadiazoles by Conventional and Non-conventional Methods)

  • Shinde, Ananta D.;Kale, Bhima Y.;Shingate, Bapurao B.;Shingare, Murlidhar S.
    • 대한화학회지
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    • 제54권5호
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    • pp.582-588
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    • 2010
  • Thiosemicarbazides의 cyclocondensation을 이용한 1,3,4-thiadiazoles, 1,3,4-triazoles과 1,3,4-oxadiazole계의 benzofuran의 합성을 좋은 수율로 합성하였다.

Facile Synthesis and Characterization of Poly(dialkoxy-p-phenylene 1,3,4-oxadiazole-alt-phenylene 1,3,4-oxadiazole)s

  • Kim, Hoon-Seok;Kang, Soon-Min;Do, Jung-Yun
    • Macromolecular Research
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    • 제16권4호
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    • pp.360-366
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    • 2008
  • Poly(dialkoxyphenylene 1,3,4-oxadiazole)s were conveniently synthesized to compare their material properties of solvent solubility, thermal stability and molecular alignment with respect to alkyl chain length and meta/para-phenylene structure. All prepared polymers exhibited good solubility in co-solvents containing various volume levels of chloroform to trifluoroacetic acid. Meta-polymers showed slightly better solubility than para-polymers. All polymers produced were thermally stable up to $320^{\circ}C$. Photoluminescence of polymer films was observed with blue light emission at around 450 nm. X-ray diffraction patterns of all polymers indicated that they were composed of stacked molecular sheets with the same layer-to-layer distance of $3.4\;{\AA}$. However, side chain-to-side chain and main chain-to-main distances within the layers increased with increasing alkyl chain lengths. The meta-polymer chains were separated more than the para-polymer chains.