22808-03-3Relevant articles and documents
Synthesis of π-conjugated copolymers composed of benzo[2,1,3]thiadiazole and thiophene units bearing various alkyl groups and their application to photovoltaic cells
Lee, Kwang-Hoi,Lee, Ho-Jin,Kuramoto, Kouji,Tanaka, Yohei,Morino, Kazuhide,Sudo, Atsushi,Okauchi, Tatsuo,Tsuge, Akihiko,Endo, Takeshi
, p. 3543 - 3549 (2011)
π-Conjugated polymers, PTOTBT, PTEHTBT, and PTt-BTBT, composed of benzothiadiazole as an electron accepting unit and terthiophene as an electron donating unit in the backbone were prepared. PTOTBT, PTEHTBT, and PTt-BTBT contained side chain groups of n-octyl, 2-ethylhexyl, and t-butyl groups, respectively. Solubility, optical and thermal properties of the polymers showed strong dependences on their side chain groups. PTEHTBT having 2-ethylhexyl groups in the side chain exhibited absorption maximum (Imax) at longer wavelength (565 nm) than PTOTBT (534 nm) and PTt-BTBT (495 nm). PTOTBT showed higher thermal stability than the others. The prepared polymers were employed to polymer solar cells (PSCs) with a configuration of ITO/PEDOT-PSS/polymer: PC61BH/LiF/Al. Power conversion efficiency of the PSC-based on PTEHTBT was 1.32%.
Synthesis of an octa-tert-butylphthalocyanine: A low-aggregating and photochemically stable photosensitizer
Gobo, Nicholas R. S.,Brocksom, Timothy J.,Zukerman-Schpector, Julio,De Oliveira, Kleber T.
, p. 5028 - 5031 (2013)
The synthesis of a new octa-tert-butylphthalocyanine is described. First, the 4,5-di-tert-butylphthalonitrile building block was synthesized in a six-step approach, in which the last step is a three reaction domino sequence. Then, this phthalonitrile was cyclotetramerized to furnish a new phthalocyanine dye, which presented no aggregation in solution and good photophysical properties. The synthesis of a new octa-tert-butylphthalocyanine is described. First, the 4,5-di-tert-butylphthalonitrile building block was synthesized in a six-step approach, in which the last step is a three reaction domino sequence. Then, this phthalonitrile was cyclotetramerized to furnish a new phthalocyanine dye, which presented no aggregation in solution and good photophysical properties. Copyright
The chemistry of the thiosulfinyl group: Preparation, structure, and spectroscopic and chemical properties of cyclic thionosulfites
Nakayama, Juzo,Yoshida, Sanae,Sugihara, Yoshiaki,Sakamoto, Akira
, p. 1451 - 1471 (2005)
Treatment of the tetrahydrothiophene-3,4-diol 5 with 1,1′-thiobis- (1H-benzimidazole) (6) furnished two diastereoisomers of the novel cyclic thionosulfite 4 with different configurations at the pseudo-tetrahedral center of the thiosulfinyl (S=S) group. The configuration of the S=S group of the major diastereoisomer (isolated in 45% yield) was established to be syn to the thiolane ring, as determined by X-ray crystallographic analysis, while that of the minor diastereoisomer (isolated in 10% yield) was anti. 1H-NMR Spectroscopic analysis clarified that the shielding and deshielding zones of the S=S group are similar to those of the well-documented S=O group. Characteristic absorptions of the S=S group in the IR, Roman, and UV/VIS spectra were assigned on the basis of calculations at the B3LYP/6-31G* level. The reactivity of the S=S group toward thermolysis, hydrolysis, and oxidation was examined. The S=S group is more resistant toward oxidation than the divalent sulfide S-atom, but is oxidatively converted to the S=O group.
So2-extrusion of an 8-thiabicylo[3.2.1]octa-2,6-diene 8,8-dioxide and rearrangement of the resulting cycloheptatriene
Takayama, Jun,Sugihara, Yoshiaki,Nakayama, Juzo
, p. 132 - 137 (2007/10/03)
The reaction of 3,4-di-tert-butylthio-phene 1-oxide (8) with tetrachlorocyclopropene provided 6,7-di-tert-butyl-2,3,4,4-tetrachloro-8-thia- bicylo[3.2.1]-octa-2,6-diene 8-oxide (10), which was oxidized to the corresponding 8,8-dioxide 16 by m-chloroperbenzoic acid. The thermolysis of 16 in refluxing chlorobenzene, xylene, or octane gave 5-tert-butyl-1,2-dichloro-3- [(1,1-dichloro-2,2-dimethyl)propyl]benzene (18) with extrusion of SO2 and 2-tert-butyl-4,5,6-trichloro-9,9-dimethylbicyclo[5.2.0]nona-1,3,5-triene (19) with extrusion of SO2 and HCl in 73-78% combined yields. On the other hand, the thermolysis of 16 in the presence of triethylamine gave 19 as the sole product in 98% yield. A mechanism that involves the initial formation of 4,5-di-tert-butyl-1,2,7,7-tetrachlorocycloheptatriene (17) is proposed to explain the observed products.