Synthesis of aryl-substituted thieno[3,2-b]thiophene derivatives and their use for N,S-heterotetracene construction

Fiesselmann thiophene synthesis was applied for the convenient construction of thieno[3,2-b]thiophene derivatives. Thus, new 5- or 6-aryl-3-hydroxythieno[3,2-b]thiophene-2-carboxylates were obtained by condensation of 5- or 4-aryl-3-chlorothiophene-2-carbox-ylates, respectively, with methyl thioglycolate in the presence of potassium tert-butoxide. The saponification of the resulting esters, with decarboxylation of the intermediating acids, gave the corresponding thieno[3,2-b]thiophen-3(2H)-ones. The latter ketones were used to synthesize new N,S-heterotetracenes, namely 9H-thieno[2',3':4,5]thieno[3,2-b]indoles by their treatment with arylhydrazines in accordance with the Fischer indolization reaction. © 2019 Demina et al.; licensee Beilstein-Institut.Russian Foundation for Basic Research, RFBR: 18-33-20083This study was supported by the Russian Foundation for Basic Research, Grant No. 18-33-20083

Synthesis, photophysical and redox properties of the 2,5,7-tri(het)aryl- [1,2,4]triazolo[1,5-a]pyrimidines

A number of Y-type push-pull compounds based on the [1,2,4]triazolo[1,5-a]pyrimidine core, namely 5,7- di(het)aryl-substituted 2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidines, were obtained by transition metal free nucleophilic C-H functionalization. Substituents at both the C-5 and C-7 positions were introduced by successive treatment of the starting 6-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine with Grignard reagents. In addition, the optical and electrochemical properties of the synthesized push-pull systems were studied. © 2020 Arkat. All rights reserved.This research study was supported financially by the Russian Science Foundation (Project No. 19-13-00234)

Microwave-Assisted synthesis and evaluation of antibacterial activity of novel 6-fluoroaryl-[1,2,4]triazolo[1,5-A]pyrimidines

A series of 6-fluoroaryl substituted [1,2,4]triazolo[1,5-A]pyrimidines have been synthesized by using the microwave-Assisted Suzuki cross-coupling reaction from readily available 6-bromo-[1,2,4]triazolo[1,5-A]pyrimidine. The antimicrobial activity of new compounds has been evaluated in vitro against Mycobacterium tuberculosis H37Rv and gram-negative (Neisseria gonorrhoeae ATCC 49226) bacteria. © ARKAT-USA, Inc

Benzo[ b]selenophene/thieno[3,2- b]indole-Based N,S,Se-Heteroacenes for Hole-Transporting Layers

Two series of new N,S,Se-heteroacenes, namely, 6H-benzo[4′,5′]selenopheno[2′,3′:4,5]thieno[3,2-b]indoles and 12H-benzo[4″,5″]selenopheno[2″,3″:4′,5′]thieno[2′,3′4,5]thieno[3,2-b]indoles, were successfully obtained using an effective strategy based on Fiesselmann thiophene and Fischer indole synthesis. The new molecules exhibit a large optical band gap (2.82 eV < Egopt < 3.23 eV) and their highest occupied molecular orbital (HOMO) energy formed by the plane π-core ranges between -5.2 and -5.6 eV, with the narrower optical band gap and lower HOMO level corresponding to selenated heteroacenes. In thin solid films of the heteroacenes, hole mobility measured using the conventional CELIV technique ranges between 10-5 and 10-4 cm2·V-1·s-1. All these make the proposed condensed-ring compounds a promising platform for the development of hole-transporting materials applicable in organic electronics. Copyright © 2020 American Chemical Society.The research (synthesis of new heteroacenes and investigation of their semiconductor properties) was financially supported by the Russian Science Foundation (project no. 18-13-00409). N.S.D. and N.A.R. would like to acknowledge the financial support for the analytical studies of synthesized compounds from the Ministry of Education and Science of the Russian Federation within the framework of the State Assignment for Research (project no. AAAA-A19-119012490006-1). The authors are grateful to Grigory A. Kim for carrying out the DFT calculations which were performed using ⟨⟨Uran⟩⟩ supercomputer of the Institute of Mathematic and Mechanics of the Ural Branch of the Russian Academy of Sciences. The XRD measurements were performed using the equipment of CKP FMI IPCE RAS

Synthesis of Regular Polyhexene in Perfluoromethylcyclohexane

This work was supported by the Russian Science Foundation (Ref. № 18-13-00365)

THERMAL CONDUCTIVITY OF FLUORINATED SOLUTIONS OF UNSATURATED HYDROCARBONS WITH A POSITIVE EXCESS VOLUME

Solutions of perfluorinated compounds and unsaturated hydrocarbons are highly nonideal systems. A decrease in the thermal conductivity of solutions relative to their additive values in the entire concentration range and their correlation with the values of excess volumes were found.Работа выполнена при финансовой поддержке РФФИ, грант № 19-38-90075