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Chulanova EA, Pritchina EA, Malaspina LA, et al. New Charge-Transfer Complexes with 1,2,5-Thiadiazoles as Both Electron Acceptors and Donors Featuring an Unprecedented Addition Reaction. Chemistry. 2016;23(4):852-864doi: 10.1002/chem.201604121.
Chulanova, E. A., Pritchina, E. A., Malaspina, L. A., Grabowsky, S., Mostaghimi, F., Beckmann, J., Bagryanskaya, I. Y., Shakhova, M. V., Konstantinova, L. S., Rakitin, O. A., Gritsan, N. P., & Zibarev, A. V. (2017). New Charge-Transfer Complexes with 1,2,5-Thiadiazoles as Both Electron Acceptors and Donors Featuring an Unprecedented Addition Reaction. Chemistry (Weinheim an der Bergstrasse, Germany), 23(4), 852-864. https://doi.org/10.1002/chem.201604121
Chulanova, Elena A, et al. "New Charge-Transfer Complexes with 1,2,5-Thiadiazoles as Both Electron Acceptors and Donors Featuring an Unprecedented Addition Reaction." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 23,4 (2017): 852-864. doi: https://doi.org/10.1002/chem.201604121
Chulanova EA, Pritchina EA, Malaspina LA, Grabowsky S, Mostaghimi F, Beckmann J, Bagryanskaya IY, Shakhova MV, Konstantinova LS, Rakitin OA, Gritsan NP, Zibarev AV. New Charge-Transfer Complexes with 1,2,5-Thiadiazoles as Both Electron Acceptors and Donors Featuring an Unprecedented Addition Reaction. Chemistry. 2017 Jan 18;23(4):852-864. doi: 10.1002/chem.201604121. Epub 2016 Dec 13. PMID: 27958639.
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Chemistry. 2017 Jan 18;23(4):852-864. doi: 10.1002/chem.201604121. Epub 2016 Dec 13.

New Charge-Transfer Complexes with 1,2,5-Thiadiazoles as Both Electron Acceptors and Donors Featuring an Unprecedented Addition Reaction.

Chemistry (Weinheim an der Bergstrasse, Germany)

Elena A Chulanova, Elena A Pritchina, Lorraine A Malaspina, Simon Grabowsky, Farzin Mostaghimi, Jens Beckmann, Irina Yu Bagryanskaya, Margarita V Shakhova, Lidia S Konstantinova, Oleg A Rakitin, Nina P Gritsan, Andrey V Zibarev

Affiliations

  1. Department of Natural Sciences, Novosibirsk State University, 630090, Novosibirsk, Russia.
  2. Institute of Organic Chemistry, Russian Academy of Sciences, 630090, Novosibirsk, Russia.
  3. Institute of Chemical Kinetics and Combustion, Russian Academy of Sciences, 630090, Novosibirsk, Russia.
  4. Institute for Inorganic Chemistry and Crystallography, University of Bremen, 28359, Bremen, Germany.
  5. Department of Physics, Novosibirsk State University, 630090, Novosibirsk, Russia.
  6. Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russia.
  7. Education and Research Center for Nanotechnology, South Ural State University, 454080, Chelyabinsk, Russia.

PMID: 27958639 DOI: 10.1002/chem.201604121

Abstract

The design and synthesis of novel charge-transfer (CT) complexes are of interest for fundamental chemistry and applications to materials science. In addition to the recently described first CT complex with both electron acceptor (A) and donor (D) groups belonging to the 1,2,5-thiadiazole series (1; A: 4-nitro-2,1,3-benzothiadiazole; D: 4-amino-2,1,3-benzothiadiazole), herein novel CT complexes 2 and 3 with 1,2,5-thiadiazoles as both A (4,6-dinitro-2,1,3-benzothiadiazole and [1,2,5]thiadiazolo[3,4-c][1,2,5]thiadiazole) and D (4-amino-2,1,3-benzothiadiazole) were synthesized. The series is completed by complex 4 with [1,2,5]thiadiazolo[3,4-c][1,2,5]thiadiazole as A and phenoxatellurine as D. Structures of complexes 2-4 were characterized by single-crystal X-ray diffraction (XRD), as well as solution and solid-state UV/Vis spectroscopy. Thermodynamics of their formation were obtained by density functional theory (DFT) calculations, their bonding situations were analyzed by quantum theory of atoms in molecules (QTAIM) calculations and dimer model energies of interactions quantified in the framework of the Hirshfeld surface (HS) analysis. With DFT calculations, the largest value of CT between D and A was found for complex 2, with 0.027 e in the XRD structure and 0.150 e in the optimized structure in MeCN. In the UV/Vis spectra, the λ

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: X-ray diffraction; chalcogens; charge transfer; donor-acceptor systems; quantum chemistry

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