The synthesis and spectral study of thiazolo[5,4-d]thiazole based small molecules using 1,3,4-oxadiazole as a linker for organic electronics

被引:2
|
作者
Balogh, Robert [1 ]
Eckstein, Anita [1 ]
Tokar, Kamil [2 ,3 ]
Danko, Martin [1 ]
机构
[1] Slovak Acad Sci, Polymer Inst, Dubravska Cesta 9, SK-84541 Bratislava, Slovakia
[2] Slovak Univ Technol Bratislava, Fac Mat Sci & Technol Trnava, Adv Technol Res Inst, Trnava 91724, Slovakia
[3] Slovak Acad Sci, Inst Phys, Dubravska Cesta 9, SK-84511 Bratislava, Slovakia
关键词
Thiazolo[5 4-d]thiazole; 1,3,4-oxadiazole; Donor; Acceptor; Band gap; Calculation; LIGHT-EMITTING DIODE; EXCITED-STATE; THIAZOLOTHIAZOLE COPOLYMER; TRANSPORTING MATERIALS; FLUORESCENCE; DERIVATIVES; ABSORPTION; HOLE;
D O I
10.1016/j.jphotochem.2022.114217
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The present research explores the experimental and theoretical study of seven new asymmetric derivatives with thiazolo[5,4-d]thiazole acceptor block and para substituted phenyl functional donor and acceptor groups linked with oxadiazole unit. We present one pot preparation of small organic molecules by simple condensation of commercially available tetrazoles and easily synthesized acyl chloride of thiazolo[5,4-d]thiazole unit. For a deeper examination of the products, UV-Vis, steady-state, and time-correlated fluorescence spectroscopy in chloroform solutions were used to study the correlation between the structure and the spectroscopic behavior of prepared compounds. The electronic properties of these derivatives were experimentally studied by cyclic vol-tammetry. The molecules were further investigated by quantum chemical calculations. It is almost certain, that studied compounds with weak electron-donor and medium to strong electron acceptor ability are not low band gap electron transport materials because UV-Vis and cyclic voltammetry results supported by the theoretical study show a wide band gap between their HOMO and LUMO orbitals. However, they may be useful in wide-bandgap semiconductors. Derivatives with electron donor moieties show low band gap and intramolecular charge transfer in the visible light region which makes them promising candidates for organic electronics. This study lays the groundwork for future research of thiazolo[5,4-d] thiazole molecules with 1,3,4-oxadiazole linkers.
引用
收藏
页数:11
相关论文
共 50 条
  • [21] Thiazolo[5,4-d]thiazole-based organic sensitizers with strong visible light absorption for transparent, efficient and stable dye-sensitized solar cells
    Dessi, Alessio
    Calamante, Massimo
    Mordini, Alessandro
    Peruzzini, Maurizio
    Sinicropi, Adalgisa
    Basosi, Riccardo
    de Biani, Fabrizia Fabrizi
    Taddei, Maurizio
    Colonna, Daniele
    di Carlo, Aldo
    Reginato, Gianna
    Zani, Lorenzo
    RSC ADVANCES, 2015, 5 (41): : 32657 - 32668
  • [22] Synthesis of a novel heterocyclic system, imidazol[1′,2′:1,2]pyrimido[5,4-d] [1,3]thiazole
    Bakavoli, M
    Khodadady, A
    Ghassemzadeh, M
    Heravi, MM
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2001, 170 : 191 - 195
  • [23] Design, Synthesis and Comprehensive Investigations of Pyrrolo[3,4-d]pyridazinone-Based 1,3,4-Oxadiazole as New Class of Selective COX-2 Inhibitors
    Szczukowski, Lukasz
    Krzyzak, Edward
    Zborowska, Adrianna
    Zajac, Patrycja
    Potyrak, Katarzyna
    Peregrym, Krzysztof
    Wiatrak, Benita
    Marciniak, Aleksandra
    Swiatek, Piotr
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2020, 21 (24) : 1 - 23
  • [24] Synthesis and Characterization of New 1,3,4-Oxadiazole Ring on Creatinine Derivatives Using Iodine and Study Their Anticancer Effect
    Ali, Rana Abid O.
    Al-Tamimi, Entesar
    Wadood, Shatha Abdul
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2023, 49 (04) : 882 - 884
  • [25] Synthesis and Characterization of New 1,3,4-Oxadiazole Ring on Creatinine Derivatives Using Iodine and Study Their Anticancer Effect
    Entesar O. Rana Abid Ali
    Shatha Abdul Al-Tamimi
    Russian Journal of Bioorganic Chemistry, 2023, 49 : 882 - 884
  • [26] Furan-bridged thiazolo [5,4-d] thiazole based D-π-A-π-D type linear chromophore for solution-processed bulk-heterojunction organic solar cells
    Nazim, M.
    Ameen, Sadia
    Akhtar, M. Shaheer
    Seo, Hyung-Kee
    Shin, Hyung-Shik
    RSC ADVANCES, 2015, 5 (09): : 6286 - 6293
  • [28] Synthesis and mesomorphism of 2,5-bis(3,4-bis(n-alkoxy)phenyl)thiazolo[5,4-d]thiazole tetracatenar liquid crystals
    Iwan, Agnieszka
    Siwy, Mariola
    Janeczek, Henryk
    Rannou, Patrice
    PHASE TRANSITIONS, 2012, 85 (04) : 297 - 308
  • [29] Highly twisted 1,3,4-oxadiazole based hybrid fluorescent organic materials: Synthesis, characterization, density functional theory calculations, and optoelectronic study
    Sharma, Deepak
    Om, Hari
    Rana, Ravi
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, 61 (09) : 1417 - 1425
  • [30] Synthesis of Carbazole-Based Polymers with 1,3,4-Oxadiazole Pendant Group and Their Application in Organic Light-Emitting Diodes
    Wang, Hui
    Ryu, Jeong-Tak
    Cao, Chao
    Kwon, Younghwan
    JOURNAL OF NANOSCIENCE AND NANOTECHNOLOGY, 2008, 8 (09) : 4846 - 4850