Research output: Contribution to journal › Article › peer-review
Synthesis, Electrochemical Reduction and Radical Anions of 2-[Bis(4-amino(nitro)phenyl)aminomethyl]-9H-thioxanthene-9-one Derivatives. / Shundrina, Inna K.; Odintsov, Danila S.; Os'kina, Irina A. et al.
In: European Journal of Organic Chemistry, Vol. 2018, No. 26, 13.07.2018, p. 3471-3480.Research output: Contribution to journal › Article › peer-review
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TY - JOUR
T1 - Synthesis, Electrochemical Reduction and Radical Anions of 2-[Bis(4-amino(nitro)phenyl)aminomethyl]-9H-thioxanthene-9-one Derivatives
AU - Shundrina, Inna K.
AU - Odintsov, Danila S.
AU - Os'kina, Irina A.
AU - Irtegova, Irina G.
AU - Shundrin, Leonid A.
PY - 2018/7/13
Y1 - 2018/7/13
N2 - 2-[Bis(4-amino(nitro)phenyl)aminomethyl]-9H-thioxanthene-9-ones and their S-oxide derivatives have been synthesized, and their electrochemical reduction (ECR) in N,N-dimethylformamide (DMF) and MeCN has been studied by cyclic voltammetry (CV). The thioxanthene-9-one group [Th(O)S] and thioxanthene-9-one S-dioxide group [Th(O)SO2] determine the first one-electron peak potentials of 2-[bis(4-aminophenyl)aminomethyl]-9H-Th(O)S/Th(O)SO2. The first peak potentials of the corresponding dinitro compounds are determined by the ratio of reduction potentials of bis(4-nitrophenyl)amino and 9H-thioxanthene-9-ones moieties. Radical anions (RA) of the synthesized compounds have been obtained by ECR in DMF and MeCN and characterized by EPR spectroscopy together with DFT calculations at the (U)B3LYP/6-31 + G/PCM level of theory. Th(O)S and Th(O)SO2 groups are thermally stable up to 270 °C. The synthesized 2-[bis(4-aminophenyl)aminomethyl]-9H-Th(O)S/Th(O)SO2 are electrochemically active monomers for subsequent synthesis of the corresponding electroactive polyimides with thioxanthene-9-one based pendant groups for their applications in the design of nonvolatile memory storage devices. The pendant groups are characterized by low redox potentials and reversibility towards electron transfer.
AB - 2-[Bis(4-amino(nitro)phenyl)aminomethyl]-9H-thioxanthene-9-ones and their S-oxide derivatives have been synthesized, and their electrochemical reduction (ECR) in N,N-dimethylformamide (DMF) and MeCN has been studied by cyclic voltammetry (CV). The thioxanthene-9-one group [Th(O)S] and thioxanthene-9-one S-dioxide group [Th(O)SO2] determine the first one-electron peak potentials of 2-[bis(4-aminophenyl)aminomethyl]-9H-Th(O)S/Th(O)SO2. The first peak potentials of the corresponding dinitro compounds are determined by the ratio of reduction potentials of bis(4-nitrophenyl)amino and 9H-thioxanthene-9-ones moieties. Radical anions (RA) of the synthesized compounds have been obtained by ECR in DMF and MeCN and characterized by EPR spectroscopy together with DFT calculations at the (U)B3LYP/6-31 + G/PCM level of theory. Th(O)S and Th(O)SO2 groups are thermally stable up to 270 °C. The synthesized 2-[bis(4-aminophenyl)aminomethyl]-9H-Th(O)S/Th(O)SO2 are electrochemically active monomers for subsequent synthesis of the corresponding electroactive polyimides with thioxanthene-9-one based pendant groups for their applications in the design of nonvolatile memory storage devices. The pendant groups are characterized by low redox potentials and reversibility towards electron transfer.
KW - Cyclic voltammetry
KW - Electrochemistry
KW - Radical ions
KW - Redox chemistry
KW - Reduction
KW - AROMATIC POLYIMIDES
KW - POLYMERS
KW - PENDANT GROUPS
KW - PERFORMANCE
KW - MEMORY DEVICES
KW - BEHAVIORS
UR - http://www.scopus.com/inward/record.url?scp=85049964434&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201800525
DO - 10.1002/ejoc.201800525
M3 - Article
AN - SCOPUS:85049964434
VL - 2018
SP - 3471
EP - 3480
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 26
ER -
ID: 15962556