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All Journal JURNAL KIMIA SAINS DAN APLIKASI Alchemy : Journal of Chemistry CHEMPUBLISH JOURNAL Al-Kimia Walisongo Journal of Chemistry Jurnal Jejaring Matematika dan Sains Jurnal Bakti Untuk Negeri Nanggroe: Journal Of Scholarly Service Nanggroe: Journal of Scholarly Service

Mokhamat Ariefin

Department Of Chemistry, Faculty Of Mathematic And Sciences, University Of Palangka Raya

Author-ID : 6268506

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Synthesis and Characterization of Pyrazine Derived Compounds as Potential Materials for Hole Transporting Layer (HTL) Vety Sri Harlinda Ayudha; Mokhamat Ariefin
Jurnal Kimia Sains dan Aplikasi Vol 23, No 6 (2020): Volume 23 Issue 6 Year 2020
Publisher : Chemistry Department, Faculty of Sciences and Mathematics, Diponegoro University

Three simple compounds that have the potential as a hole transporting layer (HTL) based on pyrazine derivatives conjugated with electron donor groups in the form of triphenylamine have been successfully synthesized and characterized. The synthesis began with a substitution reaction at high temperatures between 4-bromoaniline and 4-iodoanisole to produce 4-bromo-N,N-bis(methoxyphenyl)-aniline, followed by substitution of bromo atoms with tributylstanum at low temperatures and inert atmosphere (N2) producing 4-methoxy-N-(4-(tributylstanyl)phenyl)aniline. The conjugation reaction was carried out through a Stille coupling reaction between 1,2-bis (4-bromophenyl)ethane-1,2-dione with 4-methoxy-N-(4-(tributylstanyl)phenyl) aniline at high temperatures with the aid of a Pd(PPh3)4 catalyst in an inert atmosphere (N2). The reaction was continued with the imination reaction with 3 compounds, i.e., 1,2-diaminobenzene, 3,3-diaminobenzidine and 2,3-diaminopiridin to produce three HTL compounds that were namely 4’,4”-(quinoxaline-2,3-diyl)bis (N,N-bis(4(methoxyphenyl)-[1,1’-biphenyl]-4-amine) (DNB), 4’,4’’’,4’’’’’,4’’’’’’’-([6,6’-biquinoxaline]-2,2’,3,3’-tetrayl) tetrakis(N,N-bis(4-methoxyphenyl)- [1,1’-biphenyl] -4-amine) (bDNB), and 4’,4’’’-(pyrido[2,3-b]pyrazine-2,3-diyl)bis(N,N-bis (4-methoxyphenyl)-[1,1’-biphenyl]-4-amine) (DNP). The optical and electrochemical properties of DNB, bDNB, and DNP were analyzed by UV-Vis and Differential Pulse Voltammetry (DPV). The optical and electrochemical properties show the energy levels of the HOMO and LUMO of the three compounds. Hence their potential can be estimated as HTL compounds. The three compounds show λmax of 348 nm, 356 nm, and 350 nm for DNB, bDNB, and DNP. Based on DPV results, the HOMO values for DNB, bDNB, and DNP are -5.03 eV, -5.02 eV, and -4.98 eV and LUMO values of -2.46 eV, -2.76 eV and -2.87 eV, respectively. The three compounds' thermal properties were analyzed using TGA, with the results showing that the three compounds had good thermal resistance with a decomposition point above 400°C. Based on optical, electrochemical, and thermal analysis, DNB and bDNB have almost the same properties. Thus, it is expected that the three compounds have the potential as HTL material, with DNB and bDNB better than DNP.

Synthesis and Characterization of Benzodithiophene (BDT) Quinoid Compounds as a Potential Compound for n-Type Organic Thin-Film Transistors (OTFT) Mokhamat Ariefin; Vety Sri Harlinda Ayudha
Jurnal Kimia Sains dan Aplikasi Vol 23, No 7 (2020): Volume 23 Issue 7 Year 2020
Publisher : Chemistry Department, Faculty of Sciences and Mathematics, Diponegoro University

Two potential compounds as an n-Type organic thin-film transistor (OTFT) from benzodithiophene (BDT) derivatives have been synthesized and characterized. BDT was chosen as the core because it has π-conjugated bonds, rigid structures, and planar. Quinoid structure with end-cap (terminal group) in the form of dicyanomethylene is used because it can lower the LUMO value of the compound, and side chains are selected in the form of alkoxy so that two BDT derivatives are obtained namely BDTQ-6 (hexyloxy) and BDTQ-10 (decyloxy). Based on the results of TGA, BDTQ-6 and BDTQ-10 have decomposition points of 183°C and 203°C, which indicate the compound has excellent thermal stability. From the UV-Vis measurement, the λmax value of the two compounds is 599 nm with optical gap energy (Eg°pt) of 1.7 eV. From the DPV measurement, the LUMO value for the two compounds is -4.3 eV, with an energy gap (Eg) of 1.69 eV (BDTQ-6) and 1.70 eV (BDTQ-10). Based on observations of the crystal structure through x-ray diffraction, it was found that the BDTQ-10 crystal has a "brick type" layer arrangement with a distance between layers of 3.55 Å. With excellent thermal stability and suitable LUMO values and energy gaps, it is expected that BDTQ-6 and BDTQ-10 compounds have the potential to be n-Type OTFT materials.

Co-Authors Alfanaar, Rokiy Efriyana oksal Fatchiyatun Ni’mah Marvin Horale Pasaribu Rizki Rachmad Saputra Tety Wahyuningsih Manurung Vety Sri Harlinda Ayudha

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