Journal ArticleDOI
Impact of terminal substituents on the electronic, vibrational and optical properties of thiophene–phenylene co-oligomers
Andrey Yu. Sosorev,Andrey Yu. Sosorev,Muzaffar K. Nuraliev,Elizaveta V. Feldman,Dmitry R. Maslennikov,Dmitry R. Maslennikov,Oleg V. Borshchev,Maxim S. Skorotetcky,Nikolay M. Surin,Maxim S. Kazantsev,Sergei A. Ponomarenko,Sergei A. Ponomarenko,Dmitry Yu. Paraschuk +12 more
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TLDR
The unraveled relationships between the structure and the properties of the substituted PTTPs should facilitate a rational design of π-conjugated (co-)oligomers for efficient organic optoelectronic devices.Abstract:
Owing to the combination of efficient charge transport and bright luminescence, thiophene–phenylene co-oligomers (TPCOs) are promising materials for organic light-emitting devices such as diodes, transistors and lasers. The synthetic flexibility of TPCOs enables facile tuning of their properties. In this study, we address the effect of various electron-donating and electron-withdrawing symmetric terminal substituents (fluorine, methyl, trifluoromethyl, methoxy, tert-butyl, and trimethylsilyl) on frontier orbitals, charge distribution, static polarizabilities, molecular vibrations, bandgaps and photoluminescence quantum yields of 5,5′-diphenyl-2,2′-bithiophene (PTTP). By combining DFT calculations with cyclic voltammetry and absorption, photoluminescence, and Raman spectroscopies, we show that symmetric terminal substitution tunes the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energies of TPCOs within a range of ∼0.7 eV, shifts the frequencies of the vibrational modes associated with the phenyl rings, changes the photoluminescence quantum yield by about two-fold and slightly changes the bandgap by ∼0.1 eV. We demonstrate that these effects are governed by two factors: the Hammet constant of the substituents and their involvement in the π-conjugation/hyperconjugation described by the effective conjugation length of the substituted oligomer. A detailed picture underlying the effect of the terminal substituents on the electronic, vibrational and optical properties of TPCOs is presented. Overall, the unraveled relationships between the structure and the properties of the substituted PTTPs should facilitate a rational design of π-conjugated (co-)oligomers for efficient organic optoelectronic devices.read more
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Journal ArticleDOI
Fluorinated Thiophene-Phenylene Co-Oligomers for Optoelectronic Devices.
Andrey Yu. Sosorev,Andrey Yu. Sosorev,V.A. Trukhanov,V.A. Trukhanov,Dmitry R. Maslennikov,Dmitry R. Maslennikov,Oleg V. Borshchev,Roman A Polyakov,Maxim S. Skorotetcky,Nikolay M. Surin,Maxim S. Kazantsev,Dmitry I. Dominskiy,Dmitry I. Dominskiy,Viktor A. Tafeenko,Sergey A. Ponomarenko,Sergey A. Ponomarenko,Dmitry Yu. Paraschuk,Dmitry Yu. Paraschuk +17 more
TL;DR: This study synthesized three new fluorinated derivatives of one of the most popular TPCOs, 2,2'-(1,4-phenylene)bis[5-phenylthiophene] (PTPTP), and studied them by cyclic voltammetry, absorption, photoluminescence and Raman spectroscopies, revealing a positive effect of fluorination on the optoelectronic properties of PTPTP.
Journal ArticleDOI
Blue thermally activated delayed fluorescence emitter using modulated triazines as electron acceptors
TL;DR: In this article, three types of thermally activated delayed fluorescence (TADF) emitters are reported that emit blue-shifted emission with high external quantum efficiencies (EQEs).
Journal ArticleDOI
Synthesis, characterization and organic field-effect transistors applications of novel tetrathienoacene derivatives
Oleg V. Borshchev,Maxim S. Skorotetcky,Vasily A. Trukhanov,Vasily A. Trukhanov,Roman S. Fedorenko,Roman S. Fedorenko,Nikolay M. Surin,Evgeniya A. Svidchenko,Andrey Yu. Sosorev,Andrey Yu. Sosorev,Maxim S. Kazantsev,Dmitry Yu. Paraschuk,Dmitry Yu. Paraschuk,Sergei A. Ponomarenko +13 more
TL;DR: In this article, two novel organic semiconductors with tetrathienoacene (TTA) as the central core end-capped with 5hexyl-2-thiophene, (Hex-T)2-TTA, and 4hexylphenyl, (hex-Ph)2 -TTA have been synthesized and investigated for organic field effect transistor (OFET) applications.
Journal ArticleDOI
Selectively Fluorinated Furan-Phenylene Co-Oligomers Pave the Way to Bright Ambipolar Light-Emitting Electronic Devices
Igor P. Koskin,Christina S. Becker,Alina A. Sonina,V.A. Trukhanov,V.A. Trukhanov,Nikita A. Shumilov,Anatoly D. Kuimov,Yuliya S. Zhuravleva,Yuliya O. Kiseleva,Inna K. Shundrina,Peter S. Sherin,Dmitry Yu. Paraschuk,Dmitry Yu. Paraschuk,Maxim S. Kazantsev +13 more
Journal ArticleDOI
Crystal structure and ON-OFF polymerization mechanism of poly(1,4-phenyleneazine-N,N-dioxide), a possible wide bandgap semiconductor
Gianpiero Gallo,Gianpiero Gallo,Ana Mihanović,Igor Rončević,Robert E. Dinnebier,Hrvoj Vančik +5 more
TL;DR: In this paper, the crystal and molecular structure of poly(1,4-phenyleneazine-N, N-dioxide) (PDNB, 1) was investigated by X-ray powder diffraction (XRPD) and DFT calculations.
References
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TL;DR: The Hammett equation has been widely used for the study and interpretation of organic reactions and their mechanisms as mentioned in this paper, and it is astonishing that u constants, obtained simply from the ionization of organic acids in solution, can frequently predict successfully equilibrium and rate constants for a variety of families of reactions in solution.
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TL;DR: Electronic Coupling in Oligoacene Derivatives: Factors Influencing Charge Mobility, and the Energy-Splitting-in-Dimer Method 3.1.
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An Evaluation of Harmonic Vibrational Frequency Scale Factors
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