• Title/Summary/Keyword: Homo-coupling

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Synthesis of Dendrimers from Alkyne-focal Dendrons by Oxidative Homo-coupling of Terminal Acetylene

  • Han, Seung-Choul;Kim, Jong-Sik;Lee, Jae-Wook
    • Bulletin of the Korean Chemical Society
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    • v.32 no.11
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    • pp.3899-3903
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    • 2011
  • General, fast, and efficient fusion methods for the synthesis of dendrimers with 1,3-diynes at a core were developed. The synthetic strategy was employed the oxidative homo-coupling of terminal alkyne. The oxidative homo-coupling reaction of the alkyne-functionalized Frechet-type dendrons 1-Dm was allowed to provide first through fourth generation dendrimers 2-Gm with 1,3-diynes at core. The fusion of the propargylfunctionalized PAMAM dendrons 3-Dm by homo-coupling of terminal alkyne lead to the formation of symmetric PAMAM dendrimers 4-Gm. Their structure of dendrimers was confirmed by $^1H$ and $^{13}C$ NMR spectroscopy, IR spectroscopy, mass spectrometry, and GPC analysis.

One-Pot Homo- and Cross-Coupling Reactions of Arenediazonium Tosylate Salts for the Synthesis of Biaryls and Polyaryls

  • Vajpayee, Vaishali;Song, Young-Ho;Ahn, Jeong-Soo;Chi, Ki-Whan
    • Bulletin of the Korean Chemical Society
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    • v.32 no.spc8
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    • pp.2970-2972
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    • 2011
  • One-pot homo- and cross-coupling reactions of arenediazonium tosylate salts bearing a halogen group have been exploited for the synthesis of biaryls and polyaryls under mild conditions. $Pd(OAc)_2$ has proven to be an efficient catalyst for the successful dual transformation of diazonium salts into p-quaterphenyl (3).

Synthesis and Spectroscopic Analysis of Trans-A2B2 Metallo-Porphyrin Derivatives as Heterojunction Modulator for Organic Solar Cell

  • Jeon, Yea-Sel;Hwang, Kwang-Jin
    • Rapid Communication in Photoscience
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    • v.3 no.3
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    • pp.59-60
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    • 2014
  • The trans-$A_2B_2$ porphyrin and Ni-porphyrin derivatives were synthesized by Suzuki coupling of bromoporphyrin with arylborate as a key step. The band gaps of those complexes were measured from their absorption, emission and cyclic voltammetric data. All the LUMO energy level of porphyrin derivatives is lower than that of P3HT, and the HOMO energy level is evaluated higher than the HOMO of PCBM.

Interfacial Charge Transport Anisotropy of Organic Field-Effect Transistors Based on Pentacene Derivative Single Crystals with Cofacial Molecular Stack (코페이셜 적층 구조를 가진 펜타센 유도체 단결정기반 유기트랜지스터의 계면 전하이동 이방성에 관한 연구)

  • Choi, Hyun Ho
    • Journal of Adhesion and Interface
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    • v.20 no.4
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    • pp.155-161
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    • 2019
  • Understanding charge transport anisotropy at the interface of conjugated nanostructures basically gives insight into structure-property relationship in organic field-effect transistors (OFET). Here, the anisotropy of the field-effect mobility at the interface between 6,13-bis(triisopropylsilylethynyl) pentacene (TIPS-pentacene) single crystal with cofacial molecular stacks in a-b basal plane and SiO gate dielectric was investigated. A solvent exchange method has been used in order for TIPS-pentacene single crystals to be grown on the surface of SiO2 thin film, corresponding to the charge accumulation at the interface in OFET structure. In TIPS-pentacene OFET, the anisotropy ratio between the highest and lowest measured mobility is revealed to be 5.2. By analyzing the interaction of a conjugated unit in TIPS-pentacene with the nearest neighbor units, the mobility anisotropy can be rationalized by differences in HOMO-level coupling and hopping routes of charge carriers. The theoretical estimation of anisotropy based on HOMO-level coupling is also consistent with the experimental result.

Synthesis and Photovoltaic Properties of New π-conjugated Polymers Based on Benzo[1,2,5]thiadiazole (Benzo[1,2,5]thiadiazole을 기본 골격으로 한 공액고분자의 합성 및 광전변환특성 연구)

  • Bea, Jun Huei;Lim, Gyeong Eun;Kim, Joo Hyun
    • Applied Chemistry for Engineering
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    • v.24 no.4
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    • pp.396-401
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    • 2013
  • Alternating copolymers, poly[9-(2-octyl-dodecyl)-9H-carbazole-alt-4,7-di-thiophen-2-yl-benzo[1,2,5]thiadiazole] (PCD20TBT) and poly[9,10-bis-(2-octyl-dodecyloxy)-phenanthrene-alt-4,7-di-thiophen-2-yl-benzo[1,2,5]thiadiazole] (PN40TBT), were synthesized by the Suzuki coupling reaction. The copolymers were soluble in common organic solvents such as chloroform, chlorobenzene, 1,2-dichlorobenzene, tetrahydrofuran and toluene. The maximum absorption wavelength and the band gap of PCD20TBT were 535 nm and 1.75 eV, respectively. The maximum absorption wavelength and the band gap of PN40TBT were 560 nm and 1.97 eV, respectively. The HOMO and the LUMO energy level of PCD20TBT were -5.11 eV and -3.36 eV, respectively. As for PN40TBT, the HOMO and the LUMO energy level of PCD20TBT were -5.31 eV and -3.34 eV, respectively. The polymer solar cells (PSCs) based on the blend of copolymer and PCBM (1 : 2 by weight ratio) were fabricated. The power conversion efficiencies of PSCs based on PCD20TBT and PN40TBT were 0.52% and 0.60%, respectively. The short circuit current density ($J_{SC}$), fill factor (FF) and open circuit voltage ($V_{OC}$) of the device with PCD20TBT were $-1.97mA/cm^2$, 38.2% and 0.69 V. For PN40TBT, the $J_{SC}$, FF, and $V_{OC}$ were $-1.77mA/cm^2$, 42.9%, and 0.79 V, respectively.

Synthesis of Diaryl $\alpha$-Diketones via Palladium Catalyzed Double Carbonylative Homo Coupling of Aryl Iodides with Carbon Monoxide

  • Kim Jin Il;Kim Nam Jung;Ryu Cheol Mo
    • Bulletin of the Korean Chemical Society
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    • v.9 no.1
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    • pp.30-32
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    • 1988
  • Symmetrical diaryl ${\alpha}-diketones$ were synthesized in moderately good yields through the palladium catalyzed reaction of aryl iodides with carbon monoxide. The reaction was tolerant of a wide variety of fuctionalities($OCH_3,\;CH_3,\;NO_2,\;OH,\;COOH$) on the aryl iodide. On the other hand, the similar reaction of aryl bromides or chlorides with carbon monoxide did not proceed.

Synthesis, Photovoltaic Properties and Side-chain Effect of Copolymer Containing Phenothiazine and 2,1,3-Benzothiadiazole (Phenothiazine과 2,1,3-Benzothiadiazole을 포함한 Copolymer의 합성 및 Side-chain 치환에 따른 Photovoltaic 특성 연구)

  • Yun, Dae-Hee;Yoo, Han-Sol;Seong, Ki-Ho;Lim, Jeong-Ho;Park, Yong-Sung;Wo, Je-Wan
    • Applied Chemistry for Engineering
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    • v.25 no.5
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    • pp.487-496
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    • 2014
  • In this study, three kinds of polymers based on phenothiazine-benzothiadiazole were synthesized by a Suzuki coupling reaction, and the various side-chains were substituted at the nitrogen of phenothiazine. The optical and electrochemical properties of synthesized polymers were analyzed. The results indicate that their absorption ranged from 300 to 700 nm, and also confirmed the ideal highest occupied molecular orbital (HOMO) energy level was about -5.4 eV with low band-gap energy. Photovoltaic devices were fabricated using a photoactive layer composed of a blended solution of the polymer and $PC_{71}BM$ in ortho-dichlorobenzene The device with P2HDPZ-bTP-OBT containing the branched side-chain and long chain showed the best performance; the maximum power conversion efficiency of this device was 2.4% (with $V_{OC}$ : 0.74 V, $J_{SC}$ : $6.9mA/cm^2$, FF : 48.0%).

Synthesis and Photovoltaic Properties of Copolymer Containing Fused Donor and Difluoroquinoxaline Moieties

  • Song, Suhee;Choi, Hyo Il;Shin, In Soo;Hyun, Myung Ho;Suh, Hongsuk;Park, Seong Soo;Park, Sung Heum;Jin, Youngeup
    • Bulletin of the Korean Chemical Society
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    • v.35 no.10
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    • pp.2963-2968
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    • 2014
  • We report synthesis and photovoltaic properties of two new conjugated copolymers, PCPDTQxF and PDTSQxF, with 6,7-difluoro-2,3-dihexylquinoxaline unit prepared by Stille coupling reaction. The advantage of 6,7-difluoro-2,3-dihexylquinoxaline based copolymer are high PCEs due to lower HOMO energy level, long wavelength absorption and high hole mobility. The solid films of PCPDTQxF and PDTSQxF showed absorption bands with maximum peaks at about 623 and 493 nm and the absorption onsets at 711 and 635 nm, corresponding to band gaps of 1.74 and 1.95 eV, respectively. The oxidation onsets of the PCPDTQxF and PDTSQxF polymers were estimated to be 0.68 and 0.95 V, which correspond to HOMO energy levels of -5.48 and -5.75 eV, respectively. The PDTSQxF has lower HOMO energy level as compared to PCPDTQxF to lead higher $V_{OC}$ value. The device comprising PCPDTQxF:PCBM (1:2) dissolved to a concentration of 1 wt % in ODCB showed $V_{OC}$ value of 0.62 V, $J_{SC}$ value of $1.14mA/cm^2$, and FF of 0.35, which yielded PCE of 0.25%.

Synthesis and Photovoltaic Properties of Low Band Gap π-Cojugated Polymer Based on 4,7-Di-thiophen-2-yl-benzo[1,2,5]thiadiazole (4,7-Di-thiophen-2-yl-benzo[1,2,5]thiadiazole을 기본으로 한 고분자의 합성 및 광전변환 특성)

  • Shin, Woong;You, Hyeri;Park, Jeong Bae;Park, Sang Jun;Jeong, Mi Seon;Moon, Myung-Jun;Kim, Joo Hyun
    • Applied Chemistry for Engineering
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    • v.21 no.2
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    • pp.137-141
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    • 2010
  • Poly [4,7-Di-thiophen-2-yl-benzo(1,2,5)thiadiazole]-alt-1,4-bis(dodecyloxy)-2,5-divinylbenzene (PPVTBT) was synthesized by the Heck coupling reaction between 4,7-Di-thiophen-2-yl-benzo(1,2,5)thiadiazole and 1,4-bis(dodecyloxy)-2,5-divinylbenzene. The maximum absorption and band gap of PPVTBT were 550 nm and 1.74 eV, respectively. The HOMO and LUMO energy level of PPVTBT were -5.24 eV and -3.50 eV, respectively. The photovoltaic device based on the blend of PPVTBT and (6)-1-(3-(methoxycarbonyl)propyl)-{5}-1-phenyl[5,6]-$C_{61}$ (PCBM) (1 : 6 by weight ratio) was fabricated. The efficiency of device was 0.16%. The short circuit current density (Jsc), fill factor (FF) and open-circuit voltage (Voc) of the device was $0.74mA/cm^{2}$, 31% and 0.71 V, respectively, under AM 1.5 G and 1 sun condition ($100mA/cm^{2}$).

Synthesis and Photovoltaic Properties of Low Band Gap π-conjugated Polymers Based on 2-pyran-4-ylidene-malononitrile Derivatives (2-pyran-4-ylidene-malononitrile을 기본으로 하는 작은 Band Gap을 가지는 공중합체의 합성 및 광전변환 특성)

  • You, Hyeri;Shin, Woong;Park, Jeong Bae;Park, Sang Jun;Lim, Jun Heok;Kim, Joo Hyun
    • Applied Chemistry for Engineering
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    • v.20 no.3
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    • pp.273-278
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    • 2009
  • A series of poly[2-(2,6-dimethylpyran-4-ylidene)malononitrile-alt-1,4-bis(dodecyloxy)-2,5-divinylbenzene] (PM-PPV), poly[2-{2,6-Bis-[2-(5-bromothiophen-2-yl)-vinyl]-pyran-4-ylidene}-malononitrile-alt-1,4-bis(dodecyloxy)-2,5-divinylbenzene] (PMT-PPV) and poly[2-[2,6-Bis-(2-{4-[(4-bromophenyl)-phenylamino]-phenyl}-vinyl)-pyran-4-ylidene]-malononitrile-alt-1,4-bis(dodecyloxy)-2,5-divinylbenzene] (PMTPA-PPV) were synthesized by the Heck coupling reaction. The band gap of PM-PPV, PMT-PPV and PMTPA-PPV were 2.18 eV, 1.90 eV and 2.07 eV, respectively. The LUMO energy levels of PM-PPV, PMT-PPV and PMTPA-PPV were 3.65 eV, 3.54 eV and 3.62 eV, respectively and the HOMO energy levels of those were 5.83 eV, 5.61 eV and 5.52 eV, respectively. The photovoltaic devices based on the polymers was fabricated. The efficiency of the solar cells based on PM-PPV, PMT-PPV and PMTPA-PPV were 0.028%, 0.031% and 0.11%, respectively and the open circuit voltage (Voc) was 0.59 V~0.69 V under AM 1.5 G and 1 sun condition ($100mA/cm^2$).