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
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.
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′-