35093-32-4Relevant academic research and scientific papers
Synthesis, crystal structure, and polymerization of butterfly-shaped thieno[3,2-b]thiophene oligomers
Liu, Ying,Liu, Qida,Zhang, Xingye,Ai, Ling,Wang, Yang,Peng, Ruixiang,Ge, Ziyi
, p. 1189 - 1194 (2013)
A series of new butterfly-shaped thieno[3,2-b]thiophene oligomers with phenyl and thiophene units were synthesized through Suzuki coupling and Stille coupling reactions. The optical and thermal properties of these materials can be tuned by varying both su
Oxidation-enhanced emission: exploring novel AIEgens from thieno[3,2-b]thiophene S,S-dioxide
Chen, Bin,Zhang, Han,Luo, Wenwen,Nie, Han,Hu, Rongrong,Qin, Anjun,Zhao, Zujin,Tang, Ben Zhong
, p. 960 - 968 (2017/02/05)
Luminescent materials with high thiophene contents generally suffer from severe emission quenching in the aggregated state, owing to various active nonradiative decay channels. Herein, we report that a series of novel propeller-like luminogens consisting of a thieno[3,2-b]thiophene S,S-dioxide core and different phenyl rotors can behave oppositely. They show faint emission in solutions, but can fluoresce strongly in solid films, displaying prominent aggregation-induced emission (AIE) nature. Crystallographic, computational, and spectroscopic results reveal the synergistic effect of a propeller-like conformation and the oxidation of thieno[3,2-b]thiophene to thieno[3,2-b]thiophene S,S-dioxide greatly enhances emission efficiency of the luminogen in solid film. Calculation and electrochemical experiments reveal that they have much lower LUMO energy levels than the unoxidized counterparts. This work not only presents a feasible approach to create robust luminescent materials from thiophene by oxidation but also provides a new AIE platform with advantages of structural variety, high solid-state emission efficiency, and strong electron affinity for optoelectronic and biological applications.
1,1',2,2'-Tetrathiafulvalenes, IV. - On the Reactions of Cyclopropen(thio)nes with 1,2-Dithiole Compounds: Thienothiophenes, Thienofurans, 4H-Furopyrroles, 1,2-Dithiole-3-(thi)ones, and other Heterocycles Containing Sulfur
Behringer, Hans,Meinetsberger, Eike
, p. 315 - 341 (2007/10/02)
4,5-Disubstituted 1,2-dithiole-3-thiones (1,2-trithiones) 1 react with 2,3-diphenylcyclopropenethione (2a) to give by elimination of two atoms sulfur thienothiophenes 5.The reaction of 1a with 2a yields in addition tetraphenylthieno-1,2-dithiin (6a). 1,2-Trithiones react with 2,3-diarylcyclopropenones 7 (R3=Aryl) to give the corresponding thienofurans 8 and 1,2-dithiole-3-ones 9. - In 4-position unsubstituted 5-aryl-1,2-trithiones and 2,3-diarylcyclopropenones 7 (R3=Aryl) react in a more complex manner.In the reaction of 4,5-disubstituted 3-phenylimino-1,2-dithiole-3-thiones 18 with 7 (R3=Aryl) 4H-Furopyrroles 19 are formed. - Furthermore it will be reported on conversions of 5-phenyl-3H-1,2,4-dithiazole-3-thione (24), 2-benzyl-4-methyl-3-phenyl-1,2-thiazole-5(2H)-thione (27a), and 2-benzyl-4-phenyl-1,2-thiazole-5(2H)-thione (27b) in the reactions with the cyclopropenones 7d respective 7a.
1,1'2,2'-Tetrathiafulvalenes, III. - Syhthesis, Properties, and Reactions of 3,3'-Bi(3H-1,2-dithiolylidenes)(1,1',2,2'-Tetrathiafulvalenes)
Behringer, Hans,Meinetsberger, Eike
, p. 1928 - 1959 (2007/10/02)
1,1',2,2'-tetrathiafulvalenes 1 can be prepared by different methods from the cations of 1,2-dithiolylium salts 4 which are either unsubstituted or appropriate substituted in 3-position (instead of 3-Cl also H or SCH3).The structure of 1 is substantiated by chemical arguments.IR and 13C-NMR spectra support the absence of thioxo groups. - Like the 1,1',3,3'-isomers 2 the 1,1',2,2'-tetrathiafulvalenes are disposed to stepwise donation of electrons with formation of the radical cation and dication salts 25 or 11, respectively, as well as to the formation of charge transfer complexes with tetracyanoethylene, tetracyanoquinodimethane, and 2,3-dichloro-5,6-dicyanobenzoquinone.Tris(triphenylphosphine)rhodium(I) chloride and tetrakis(triphenylphosphine)platinum(O) yield complexes with 1a. - Thermolysis of 1 produces thienothiophenes 6.Partial desulfuration of 1a, for example, is also feasible with oxidizing agents like lead(IV) acetate.Selenium dioxide, however, gives the corresponding thienofuran 41.The reaction with trialkyl phosphites yields a disulfide - probably the 2,2'-bi(2H-thietylidene) 38 - the thermolysis of which gives the thienothiophene 6a. - Compounds 1a and 1c do not react with dimethyl acetylenedicarboxylate, isothiocyanate, several 1,3-dipoles (azides), and also not with elementary sulfur, however, 1e forms with sulfur the 3H-1,2-dithiol-3-thione 5e (X = S).
1,1',2,2'-Tetrathiafulvalenes, II. - Thienothiophenes from 1,2-Dithiole Compounds; 3H-1,2-Dithiol-3-ylidenes (1,2-Dithiole-3-carbenes) as Supposed Intermediates
Behringer, Hans,Meinetsberger, Eike
, p. 1729 - 1750 (2007/10/02)
3,3'-Bi(3H-1,2-dithiolylidenes) (1,1',2,2'-Tetrathiafulvalenes) 5 are not obtainable with the following reactions which, however, have proved to be a good approach to the corresponding 1,3-isomers 3: 1) Deprotonation of 1,2-dithiolylium cations 4, 2) pyrolysis of alkali derivatives from 1,2-dithiol-2-one tosylhydrazones 26 (Bamford-Stevens reaction), or 3) partial desulfuration of 1,2-dithiole-3-thiones 6 by means of trivalent phosphorus compounds.These reactions with the 1,2-isomers always yield thienothiophenes 8 accompanied by the related 1,2-dithiole-3-thiones 6 (1,2-trithiones) and in the case of 26 also by azines 27.Partial desulfuration of 1,2-trithiones 6 by copper bronze again yields the corresponding thienothiophenes 8 instead of 5.Thermal decomposition of the 1,2-dithiolylium iodide 34 or 34' yields the thienothiophene 8a together with the 1,2-trithione 6a.Surprisingly, the P4S10-sulfuration of "desaurines" 37 gives thienothiophenes again and also 1,2-dithiole-3-thiones 6. - 1-Morpholinocyclohexene (18) reacts with the 1,2-dithiolylium cation 4a (X = ClO4) to give a formal 1:1 adduct from the carbene 9a and the enamine for which the structure 19 is proposed.
