4388-22-1Relevant articles and documents
Bis[1]benzothieno[1,4]thiazines: Planarity, Enhanced Redox Activity and Luminescence by Thieno-Expansion of Phenothiazine
Schneeweis, Arno P. W.,Hauer, Simone T.,Reiss, Guido J.,Müller, Thomas J. J.
, p. 3582 - 3590 (2019)
Twofold Buchwald–Hartwig aminations selectively furnish three regioisomers of bis[1]benzothieno[1,4]thiazines; X-ray structure analyses and DFT calculations were corroborated for correlation of their electronic properties. All regioisomers outscore the pa
A convenient and improved synthesis of dithieno[3,2-b:2′,3′-d]thiophene
Allared, Fredrik,Hellberg, Jonas,Remonen, Tommi
, p. 1553 - 1554 (2002)
An improved synthesis of dithieno[3,2-b:2′,3′-d]thiophene 1 is presented. By starting from 2,3-dibromothiophene 2 the total yield was improved from 35 to 58%. We also describe a more convenient synthesis of one of the reagents, benzenesulfonic acid thioanhydride 3.
3,9-Disubstituted Bis[1]benzothieno[3,2-b;2′,3′-e][1,4]thiazines with Low Oxidation Potentials and Enhanced Emission
Berens, Henning R. V.,Mohammad, Kausar,Reiss, Guido J.,Müller, Thomas J. J.
, p. 8000 - 8014 (2021)
Dibrominated bis[1]benzothieno[3,2-b;2′,3′-e][1,4]thiazines (BBTT) are efficiently synthesized and applied in Suzuki and Buchwald-Hartwig cross-coupling reactions to give access to 3,9-disubstituted BBTT derivatives with extended π-conjugation and enhanced electronic properties. For instance, 3,9-di(hetero)aryl substituted BBTT derivatives surpass their parent congeners phenothiazines with lower oxidation potentials and pronounced yellow to orange-red fluorescence (φf ≈ 30-45%). In addition, 3,9-bis(di(hetero)arylamino substituted BBTT possess very high lying HOMO energy (EHOMO =-4.46 to-4.83 eV), a favorable property of hole transport molecules. A representative X-ray structure analysis reveals that the central BBTT core in these extended π-systems is essentially planarized. Upon protonation of a 3,9-bis(di(hetero)arylamino) substituted BBTT, the absorption color shifts from yellow to deep blue with a concomitant loss of the emission. The optical properties of these novel BBTT derivatives can be plausibly rationalized by time-dependent density functional theory (TD(DFT)) calculations and correlation between experimentally determined oxidation potentials and σp parameters as well as between photophysical data and the specific substituent parameter σp- by establishing electronic structure-property relationships.
Selective Metalations of 1,4-Dithiins and Condensed Analogues Using TMP-Magnesium and -Zinc Bases
Castelló-Micó, Alicia,Nafe, Julia,Higashida, Kosuke,Karaghiosoff, Konstantin,Gingras, Marc,Knochel, Paul
supporting information, p. 360 - 363 (2017/04/21)
TMPMgCl·LiCl and TMPZnCl·LiCl allow facile magnesiation and zincation, respectively, of the 1,4-dithiin scaffold, producing polyfunctionalized 1,4-dithiins. A subsequent metalation of these S-heterocycles can also be achieved with the same TMP bases, lead
4H-Dithieno[2,3-b:3′,2′-e][1,4]thiazines - Synthesis and electronic properties of a novel class of electron rich redox systems
Dostert, Catherine,Wanstrath, Claudia,Frank, Walter,Mueller, Thomas J. J.
supporting information; experimental part, p. 7271 - 7273 (2012/08/13)
Quantum chemical screening reveals that 4H-dithieno[2,3-b:3′, 2′-e][1,4]thiazines possess the highest HOMO among four constitutional isomers, even 0.27 eV higher in energy than the well established 10H-phenothiazine. N-Substituted 4H-dithieno[2,3-b:3′,2′-
OLIGOTHIOPHENES AND SYNTHESIS THEREOF
-
, (2008/06/13)
Novel oligothiophenes and intermediates therefor are disclosed together with a process for synthesizing them. The oligothiophenes are in the form of a helix which contains five-membered rings unsaturated heterocycles that are cross-conjugated and annelated into a helix.
Synthesis, polymerization and characterization of substituted dithieno [3,4-b: 3',4'-d] thiophenes
Inaoka, Seiji,Collard, David M.
, p. 1719 - 1725 (2007/10/03)
Chemical or electrochemical oxidation of substituted dithieno [3,4- b:3',4'-d]thiophenes provides polymers with defined regiochemical structures. These materials have lower bandgaps (0.7-0.9 eV) than the unsubstituted fused heteroarene. Potential cycling of the 1,3-dimethyl substituted polymer film shows repetitive p- and n-dopability. The chemically-prepared dioctyl analog is soluble in common solvents such as chloroform, dichloromethane and THF. However, overoxidation of the polymers at an electrode surface presents a limitation to the polymerization of substituted analogs of the parent fused heteroarene.
A Catalytic Effect of Amines on the Reaction of Arenesulfinic Acids with N,N'-Thiodiphthalimide
Abe, Yasuo,Horii, Toyokazu,Oka, Kunio,Kawamura, Shunichi,Nakabayashi, Takeshige
, p. 3678 - 3682 (2007/10/02)
In the presence of catalytic amounts of several amines, N,N'-thiodiphthalimide has been allowed to react with one or two equiv. of arenesulfinic acids in dichloromethane, thus giving N-(arylsulfonylthio)phthalimides or bis(arenesulfonyl) sulfides respectively in good yields.The arenesulfinate anion seems to be a better nucleophile against N,N'-thiodiphthalimide than arenesulfinic acid.The mechanism of the catalytic reaction will be discussed.
