DFT study on some polythiophenes containing benzo[d]thiazole and benzo[d]oxazole: structure and band gap

References

• Ikai T, Takayama K, Wada Y, et al. Synthesis of a one-handed helical polythiophene: a new approach using an axially chiral bithiophene with a fixed syn-conformation. Chem Sci. 2019;10(18):4890–4895.
   PubMed Web of Science ®Google Scholar
• Valderrama-García B, Rodríguez-Alba E, Morales-Espinoza E, et al. Synthesis and characterization of novel polythiophenes containing pyrene chromophores: thermal, optical and electrochemical properties. Molecules. 2016;21(2):172.
   PubMed Web of Science ®Google Scholar
• Pina J, Beltran Rodrigues AC, Alnady MMSA, et al. Restricted aggregate formation on tetraphenylethene-substituted polythiophenes. J Phys Chem C. 2020;124(25):13956–13965.
   Web of Science ®Google Scholar
• Gupta S, Chatterjee S, Zolnierczuk P, et al. Impact of local stiffness on entropy driven microscopic dynamics of polythiophene. Sci Rep. 2020;10(1):9966.
   PubMed Web of Science ®Google Scholar
• Langeveld-Voss BMW, Janssen RAJ, Meijer EW. On the origin of optical activity in polythiophenes. J Mol Struct. 2000;521(1–3):285–301.
   Google Scholar
• Kaloni TP, Giesbrecht PK, Schreckenbach G, et al. Polythiophene: from fundamental perspectives to applications. Chem Mater. 2017;29(24):10248–10283.
   Web of Science ®Google Scholar
• Hu Z, Zhang S, Zhang C, et al. Donor–acceptor units modulate the electronic and photoluminescence characteristics of thiophene oligomers. J Appl Phys. 2019;126(24):245501.
   Web of Science ®Google Scholar
• Nguyen NL, Tran TTD, Nguyen H, et al. Synthesis of polythiophene containing heterocycle on the side chain: a review. Vietnam J. Chem. 2020;58(1):1–9.
   Google Scholar
• Djemoui A, Naouri A, Ouahrani MR, et al. A step-by-step synthesis of triazole-benzimidazole-chalcone hybrids: anticancer activity in human cells+. J Mol Struct. 2020;1204:127487.
   Web of Science ®Google Scholar
• Tokárová Z, Maxianová P, Váry T, et al. Thiophene-centered azomethines: structure, photophysical and electronic properties. J Mol Struct. 2020;1204:127492.
   Web of Science ®Google Scholar
• Vu QT, Tran TTD, Dang TT, et al. Some chalcones derived from thiophene-3-carbaldehyde: synthesis and crystal structures. Acta Cryst. Section E. 2019;75(7):957–963.
   Google Scholar
• Esquivel ECC, Rufino VC, Nogueira MHT, et al. Synthesis and characterization of 1,3,5-triarylpyrazol-4-ols and 3,5-diarylisoxazol-4-ols from chalcones and theoretical studies of the stability of pyrazol-4-ol toward acid dehydration. J Mol Struct. 2020;1204:127536.
   Web of Science ®Google Scholar
• Levesque I, Bazinet P, Roovers J. Optical properties and dual electrical and ionic conductivity in Poly(3-methylhexa(oxyethylene)oxy-4-methylthiophene). Macromolecules. 2000;33(8):2952.
   Web of Science ®Google Scholar
• Ming S, Youjun H, Kunlun H, et al. A water-soluble polythiophene for organic field-effect transistors. Polym Chem. 2013;4(20):5270–5274.
   Web of Science ®Google Scholar
• Pei J, Yu WL, Ni J, et al. Thiophene-based conjugated polymers for light-emitting diodes:  effect of aryl groups on photoluminescence efficiency and redox behavior. Macromolecule. 2001;34(21):7241.
   Web of Science ®Google Scholar
• Snook GA, Kao P, Best AS. Conducting-polymer-based supercapacitor devices and electrodes. J Power Sources. 2011;196(1):1–12.
   Web of Science ®Google Scholar
• Ghaitaoui T, Ali B, Sahli Y, et al. Realization and characterization of p-typed polythiophene based organic photovoltaic cells. Journal of Nano- and Electronic Physics. 2018;10(1):01008.
   Google Scholar
• Nabasmita M, Radhakanta G, Arun Nandi K. Optoelectronic properties of self-assembled nanostructures of polymer functionalized polythiophene and graphene. Langmuir. 2018;34(26):7585–7597.
   PubMed Web of Science ®Google Scholar
• Borrelli DC, Lee S, Gleason KK. Optoelectronic properties of polythiophene thin films and organic TFTs fabricated by oxidative chemical vapor deposition. Journal of Materials Chemistry C. 2014;2(35):7223–7231.
   Web of Science ®Google Scholar
• Sandip D, Dhruba PC, Radhakanta G, et al. Water soluble polythiophenes: preparation and applications. RSC Adv. 2015;5(26):20160–20177.
   Web of Science ®Google Scholar
• Maiti J, Pokhrel B, Boruah R, et al. Polythiophene based fluorescence sensors for acids and metal ions. Sens Actuators B Chem. 2009;141(2):447–451.
   Web of Science ®Google Scholar
• Wang F, Li M, Wang B, et al. Synthesis and characterization of water-soluble polythiophene derivatives for cell imaging. Sci Rep. 2015;5(1):7617.
   PubMedGoogle Scholar
• Aldo VA, Gerardo ZG, Edgar AO, et al. Luminescent polythiophenes-containing porphyrin units: synthesis, characterization, and optical properties. Designed Monomers & Polymers. 2014;17(1):78–88.
   Web of Science ®Google Scholar
• Kambiz S, Jeong-Yeol Y, Jongchul S, et al. Chromogenic polymers and their packaging applications: a review. Polymer Rev. 2020;60(3):442–492.
   Web of Science ®Google Scholar
• Elbing M, Garcia A, Urban S, et al. In Situ conjugated polyelectrolyte formation. Macromolecules. 2008;41(23):9146–9155.
   Web of Science ®Google Scholar
• Aiello S, Wells G, Stone EL, et al. Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648). J Med Chem. 2008;51(16):5135–5139.
   PubMed Web of Science ®Google Scholar
• Cho Y, Ioerger TR, Sacchettini JC. Discovery of novel nitrobenzothiazole inhibitors for mycobacterium tuberculosis ATP phosphoribosyl transferase (HisG) through virtual screening. J Med Chem. 2008;51(19):5984–5992.
   PubMed Web of Science ®Google Scholar
• Radhakrishnan S, Parthasarathi R, Subramanian V, et al. Structure and properties of polythiophene containing hetero aromatic side chains. Comput Mater Sci. 2006;37(3):318–322.
   Web of Science ®Google Scholar
• Radhakrishnan S, Somanathan N. Poly(thiophenes) functionalised with thiazole heterocycles as electroluminescent polymers. J Mater Chem. 2006;16(29):2990–3000.
   Web of Science ®Google Scholar
• Radhakrishnan S, Somanathan N, Thelakkat M. Thermal degradation studies of polythiophenes containing hetero aromatic side chains. Int J Thermophys. 2009;30(3):1074–1108.
   Web of Science ®Google Scholar
• Esashika K, Yoshizawa-Fujita M, Takeoka Y, et al. Synthesis and optical properties of poly(thiophene-fluorene) copolymers with benzothiazole moiety. Synth Met. 2009;159(21–22):2184–2187.
   Web of Science ®Google Scholar
• Nguyen NL, Vu QT, Duong QH, et al. Green synthesis and crystal structure of 3-(benzo-thia-zol-2-yl)thio-phene, Acta crystallographica. Section E, Crystallographic communications. 2017;73(11):1647–1651.
   PubMedGoogle Scholar
• Radhakrishnan S, Parthasarathi R, Subramanian V, et al. Quantum chemical studies on polythiophenes containing heterocyclic substituents: effect of structure on the band gap. J Chem Phys. 2005;123(16):164905.
   PubMed Web of Science ®Google Scholar
• Thaneshwor PK, Georg S, Michael SF. Band gap modulation in polythiophene and polypyrrole-based systems. Sci Rep. 2016;6(1):36554.
   PubMedGoogle Scholar
• Arnold CA, Wilfredo CC, Rolando VB, et al. AB initio and density functional studies of polythiophene energy band gap. NECTEC Technical Journal. 2001;9:215–218.
   Google Scholar
• Brocks G. Density functional study of polythiophene derivatives. J Phys Chem. 1996;100(43):17327–17333.
   Web of Science ®Google Scholar
• Si MB, Guillermo SM, Mohamed H, et al. DFT study of polythiophene energy band gap and substitution effects. J Chem. 2015;9:12. Article ID 296386
   Google Scholar
• Ali SR, Mehri E, Etesam G, et al. The polythiophene molecular segment as a sensor model for H2O, HCN, NH3, SO3, and H2S: a density functional theory study. J Mol Model. 2016;22(6):127. 8
   PubMed Web of Science ®Google Scholar
• Anusuya S, Bishwajit G. A DFT study to probe homo-conjugated norbornylogous bridged spacers in dye-sensitized solar cells: an approach to suppressing agglomeration of dye molecules. RSC Adv. 2020;10(26):15307–15319.
   Web of Science ®Google Scholar
• Nguyen NH, Ngo TC, Hoang VH, et al. Electronic properties of the polypyrrole-dopant anions <sub>ClO4 − and <sub>MoO42−: a density functional theory study. J Mol Model. 2017;23(12):336.
   PubMed Web of Science ®Google Scholar
• Muhammad AA, Shaikh M, Fatma K, et al. Synthesis and characterization of poly(3-hexylthiophene): improvement of regioregularity and energy band gap. RSC Adv. 2018;8(15):8319–8328.
   Web of Science ®Google Scholar
• Vu QT, Tran TTD, Nguyen TC, et al. DFT prediction of factors affecting the structural characteristics, the transition temperature and the electronic density of some new conjugated polymers. Polymers. 2020;12(6):1207.
   Web of Science ®Google Scholar
• Rittmeyer SP, Gro A. Structural and electronic properties of oligo- and polythiophenes modified by substituents, Beilstein J. Nanotechnol 2012;3:909–919.
   Web of Science ®Google Scholar
• Banjo S, Ayobami OO, Ajibade AI. Structural and electronic properties of 4H-cyclopenta[2,1-b,3;4-b′]dithiophene S-oxide (BTO) derivatives with an S, S=O, O, SiH2, or BH2 bridge: semi-empirical and DFT study. J Mol Model. 2011;18(6):2755–2760.
   PubMed Web of Science ®Google Scholar
• Lo PK, Lau KC. High-level ab initio predictions for the ionization energies and heats of formation of five-membered-ring molecules: thiophene, Furan, Pyrrole, 1,3-Cyclopentadiene, and Borole, C4H4X/C4H4X+(X = S, O, NH, CH2, and BH). J Phys Chem A. 2011;115(5):932–939.
   PubMed Web of Science ®Google Scholar
• Barlow S, Odom SA, Lancaster K, et al. Electronic and optical properties of 4H-Cyclopenta[2,1-b:3,4-b′]bithiophene derivatives and their 4-Heteroatom-substituted analogues: a joint theoretical and experimental comparison. J Phys Chem A. 2010;114(45):14397–14407.
   Web of Science ®Google Scholar
• Kien PH, Lan MT, Dung NT, et al. Annealing study of amorphous bulk and nanoparticle iron using molecular dynamics simulation. Int J Modern Phys B. 2014;28(23):1450155. 17
   Web of Science ®Google Scholar
• Trong DN, Chinh CN, The TN, et al. Factors on the magnetic properties of the iron nanoparticles by classical heisenberg model. Physica B. 2018;532:144–148.
   Web of Science ®Google Scholar
• Nguyen-Trong D, Nguyen-Tri P. Understanding the heterogeneous kinetics of Al nanoparticles by simulations method. J Mol Struct. 2020;1218(9):128498.
   Google Scholar
• Quoc TT, Trong DN. Molecular dynamics factors affecting on the structure, phase transition of Al bulk. Phys B Condens Matter. 2019;570:116–121.
   Web of Science ®Google Scholar
• Quoc TT, Trong DN, tefan S¸, et al. Study on the influence of factors on the structure and mechanical properties of amorphous aluminium by molecular dynamics method. Adv Mater Sci Eng. 2021;2021(10):5564644.
   Google Scholar
• Nguyen TD, Nguyen CC, Hung Tran V. Molecular dynamics study of microscopic structures, phase transitions and dynamic crystallization in Ni nanoparticles. RSC Adv. 2017;7(41):25406–25413.
   PubMed Web of Science ®Google Scholar
• NguyenTrong D. Z-AXIS deformation method to investigate the influence of system size, structure phase transition on mechanical properties of bulk nickel. Mater Chem Phys. 2020;252(6):123275.
   Google Scholar
• Dang Thi Minh H, Coman G, Nguyen Quang H, et al. Influence of heating rate, temperature, pressure on the structure, and phase transition of amorphous Ni material: a molecular dynamics study. Heliyon. 2020;6(11):e05548.
   PubMed Web of Science ®Google Scholar
• Trong DN, Chinh CN, Quoc VD, and Tuan Tran Quoc. Study the effects of factors on the structure and phase transition of bulk Ag by molecular dynamics method. International Journal of Computational Materials Science and Engineering. 11. 2020;9(3):2050016.
   Web of Science ®Google Scholar
• Nguyen-Trong D, Nguyen-Tri P. Factors affecting the structure, phase transition and crystallization process of AlNi nanoparticles. J Alloys Compd. 2020;812(8):152133.
   Google Scholar
• Nguyen-Trong D, Nguyen-Tri P. Molecular dynamic study on factors influencing the structure, phase transition and crystallization process of NiCu6912 nanoparticle. Mater Chem Phys. 2020;250(6):123075.
   Google Scholar
• Tuan TQ, Dung NT. Effect of heating rate, impurity concentration of Cu, atomic number, temperatures, time annealing temperature on the structure, crystallization temperature and crystallization process of Ni1-xCux bulk; x = 0.1, 0.3, 0.5, 0.7”. Int J Modern Phys B. 2018;32(26):1830009. 15
   Web of Science ®Google Scholar
• Nguyen-Trong D, Pham-Huu K, Nguyen-Tri P. Simulation on the factors affecting the crystallization process of FeNi alloy by molecular dynamics. ACS Omega. 2019;4(11):14605–14612.
   PubMed Web of Science ®Google Scholar
• Trong Dung N. Influence of impurity concentration, atomic number, temperature and tempering time on microstructure and phase transformation of Ni1−xFex (x= 0.1, 0.3, 0.5) nanoparticles. Mod Phys Lett B. 2018;32(18):1850204. 14
   Web of Science ®Google Scholar
• Van Cao L, Van Duong Q, Nguyen Trong D. Ab Initio Calculations on the structural and electronic properties of AgAu Alloys. ACS Omega. 2020;5(48):31391–31397.
   PubMed Web of Science ®Google Scholar
• Trong DN, Long VC, Ţălu S. The structure and crystal-lizing process of NiAu alloy: a molecular dynamics simulation method. J Composites Sci. 2021;5(1):1–14.
   Google Scholar
• Quoc TV, La Trieu D, Van Duong Q, et al. Effect of doped H, Br, Cu, Kr, Ge, As and Fe on structural features and bandgap of poly C13H8OS-X: a DFT calculation. Des Monomers Polym. 2021;24(1):53–62.
   PubMed Web of Science ®Google Scholar
• Arjunan V, Thirunarayanan S, Durga DG, et al. Substituent influence on the structural, vibrational and electronic properties of 2,5-dihydrothiophene-1,1-dioxide by experimental and DFT methods. Spectrochim Acta A Mol Biomol Spectrosc. 2015;150:641–651.
   PubMed Web of Science ®Google Scholar
• Yılmaz ZT, Yasin Odabaşoğlu H, Şenel P, et al. A novel 3-((5-methylpyridin-2-yl)amino)isobenzofuran-1(3H)-one: molecular structure describe, X-ray diffractions and DFT calculations, antioxidant activity, DNA binding and molecular docking studies. J Mol Struct. 2020;1205:127585.
   Web of Science ®Google Scholar
• Prabavathi N, Senthil NN, Venkatram RB. Molecular structure, vibrational spectra, natural bond orbital and thermodynamic analysis of 3,6-dichloro-4-methylpyridazine and 3,6-dichloropyridazine-4-carboxylic acid by DFT approach. Spectrochim Acta A Mol Biomol Spectrosc. 2015;136:1134–1148.
   PubMed Web of Science ®Google Scholar
• Kantchev EAB, Norsten TB, Tan MLY, et al. Thiophene-containing pechmann dyes and related compounds: synthesis, and experimental and DFT characterisation. Chem A Eur J. 2011;18(2):695–708.
   PubMed Web of Science ®Google Scholar
• Thaneshwor PK, Georg S, Michael SF. Band gap modulation in polythiophene and polypyrrole-based systems. Sci Rep. 2016;6(1):36554.
   PubMedGoogle Scholar
• Fréchette M, Belletete M, Bergeron J-Y, et al. Monomer reactivity vs regioregularity in polythiophene derivatives: a joint synthetic and theoretical investigation. Synth Met. 1997;84(1–3):223–224.
   Web of Science ®Google Scholar
• Sun H, Autschbach J. Electronic energy gaps for π-conjugated oligomers and polymers calculated with density functional theory. J Chem Theory Comput. 2014;10(3):1035–1047.
   PubMed Web of Science ®Google Scholar
• Hussain M, Arshad N, Ujan R, et al. Synthesis, structure elucidation and surface analysis of a new single crystal N-((2-(benzo [4,5]imidazo [1,2-c]quinazolin-6-yl)phenyl)carbamothioyl)heptanamide: theoretical and experimental DNA binding studies. J Mol Struct. 2020;1205:127496.
   Web of Science ®Google Scholar
• Delley B. An all-electron numerical method for solving the local density functional for polyatomic molecules. J Chem Phys. 1990;92(1):508–517.
   Web of Science ®Google Scholar
• Delley B. From molecules to solids with the DMol3 approach. J Chem Phys. 2000;113(18):7756–7764.
   Web of Science ®Google Scholar
• Perdew JP, Burke K, Ernzerhof M. Generalized gradient approximation made simple. Phys Rev Lett. 1996;77(18):3865–3868.
   PubMed Web of Science ®Google Scholar
• Tsuzuki S, Lüthi HP. Interaction energies of van der Waals and hydrogen bonded systems calculated using density functional theory: assessing the PW91 model. J Chem Phys. 2001;114(9):3949.
   Web of Science ®Google Scholar
• Perdew JP, Wang Y. Accurate and simple analytic representation of the electron-gas correlation energy. Phys Rev B. 1992;45(23):13244–13249.
   PubMed Web of Science ®Google Scholar
• Monkhorst HJ, Pack JD. Special points for Brillouin-zone integrations. Phys Rev B. 1976;13(12):5188–5192.
   Web of Science ®Google Scholar