241-13-4Relevant academic research and scientific papers
Optical properties of dibenzo[d,d′]thieno[3,2-b;4,5-b′] dithiophene monocrystals: The effect of intermolecular interactions
Alessandrini, Laura,Braga, Daniele,Jaafari, Abdelhafid,Miozzo, Luciano,Mora, Stefano,Silvestri, Leonardo,Tavazzi, Silvia,Yassar, Abderrahim
, p. 225 - 231 (2011)
The polarized UV-visible absorption spectra of dibenzo[d,d′]thieno[3, 2-b;4,5-b′]dithiophene single crystals are reported and interpreted to definitively attribute the observed bands and their polarizations. The results provide information on the intermolecular interactions and on the aggregation in the condensed phase, which can be of either herringbone- or H-type, depending on the electronic transition taken into considerations, with consequences on the order and polarization of the absorption bands. A relatively easy method is also discussed to obtain information on the structural/morphological properties of different types of samples, including thin films, which have been recently proposed for high-performance organic film-effect transistors for their high ionization potential and photostability.
Ambidextrous catalytic access to dithieno[3,2- b:2′,3′- d ]thiophene (DTT) derivatives by both palladium-catalyzed C-S and oxidative dehydro C-H coupling
Oechsle, Peter,Paradies, Jan
, p. 4086 - 4089 (2014)
A modular two-step synthesis of dithieno[3,2-b:2′,3′-d] thiophene (DTT) derivatives by C-S cross-coupling and oxidative dehydro C-H coupling is herein described. Dibenzo[d,d′]thieno[3,2-b;4,5-b′] dithiophene (DBTDT) and associated two donor (anisyl) and a
Electrochemical Synthesis of Thienoacene Derivatives: Transition-Metal-Free Dehydrogenative C?S Coupling Promoted by a Halogen Mediator
Mitsudo, Koichi,Matsuo, Ren,Yonezawa, Toki,Inoue, Haruka,Mandai, Hiroki,Suga, Seiji
, p. 7803 - 7807 (2020/04/15)
The first electrochemical dehydrogenative C?S bond formation leading to thienoacene derivatives is described. Several thienoacene derivatives were synthesized by dehydrogenative C?H/S?H coupling. The addition of nBu4NBr, which catalytically promoted the reaction as a halogen mediator, was essential.
Cyclization of 2-Biphenylthiols to Dibenzothiophenes under PdCl2/DMSO Catalysis
Zhang, Tao,Deng, Guigang,Li, Hanjie,Liu, Bingxin,Tan, Qitao,Xu, Bin
, p. 5439 - 5443 (2018/09/13)
A palladium-catalyzed synthesis of dibenzothiophenes from 2-biphenylthiols is described. This highly efficient reaction employs a simple PdCl2/DMSO catalytic system, in which PdCl2 is the sole metal catalyst and DMSO functions as an oxidant and solvent. This transformation has broad substrate scope and operational simplicity and proceeds in high yield. The synthetic utility was demonstrated by the facile synthesis of helical dinapthothiophene 3 and an eminent organic semiconductor DBTDT 4. Importantly, highly strained trithiasumanene 5, a buckybowl of considerable synthetic challenge, was observed under this catalytic system.
Linear and Angular Heteroacenes from Double-Electrophilic Cyclization (DEC) and DEC-Reductive Elimination of Diynes
Gupta, Akhil,Flynn, Bernard L.
, p. 1939 - 1941 (2017/04/28)
Linear and angular heteroacenes are prepared from terminal alkynes bearing tethered nucleophiles in two steps. Linear heteroacenes are formed from the homocoupling of these alkynes followed by reaction with a double electrophile (ECl2) to induce a tricyclization reaction cascade involving double-electrophilic cyclization (DEC). Related angular heteroacenes are formed from the prior substitution of the chloro groups in ECl2 with the same terminal alkyne followed by reaction with AuCl3 to produce a DEC-reductive-elimination (DECRE) reaction.
Synthesis of chalcogenophenes via cyclization of 1,3-diynes promoted by Iron(III) chloride and dialkyl dichalcogenides
Bilheri, Filipe N.,Stein, André L.,Zeni, Gilson
supporting information, p. 1221 - 1228 (2015/04/22)
In this paper, we report the iron(III) chloride and dibutyl diselenide-mediated cyclization of 1,3-diynes which leads to 3,4-bis(butylselanyl)selenophenes. The optimization studies showed that the reaction was best performed with equimolar amounts of iron(III) chloride and dibutyl diselenide in dichloromethane at 40C for 4h. The method allows the synthesis of symmetrical and unsymmetrical selenophenes in moderate to good yields. A similar protocol was also extended to the synthesis of thiophene derivatives using dimethyl disulfide instead of dibutyl diselenide. The resulting selenophenes and thiophenes were further functionalized by selenium-halogen exchange reactions, Sonogashira cross-coupling reactions and electrophilic cyclizations.
Lewis acid/Broensted acid mediated benz-annulation of thiophenes and electron-rich arenes
Rafiq, Settu Muhamad,Sivasakthikumaran, Ramakrishnan,Mohanakrishnan, Arasambattu K.
supporting information, p. 2720 - 2723 (2014/06/09)
A facile preparation of benz-annulated heterocycles were achieved at rt involving a Lewis acid/Broensted acid mediated annulation of heterocycles using 2,5-dimethoxytetrahydrofuran as a four-carbon synthon. The benz-/naphth-annulation was found to be successful with electron-rich arenes as well.
ORGANIC SEMICONDUCTOR COMPOUNDS
-
, (2012/02/01)
The disclosure is related to organic semiconductor compounds including benzodithieno(3,2-b:2′,3′-d)thiophene (BDTT) and the derivatives of benzodithieno(3,2-b:2′,3′-d)thiophene. The organic compounds of the disclosure have high resistance to the oxidation and high electrical stability. Accordingly, the semiconductor device having an organic semiconductor layer made of the organic compounds of the disclosure has stable electrical performance, and the reliability of the semiconductor device is improved.
General synthesis of thiophene and selenophene-based heteroacenes
Okamoto, Toshihiro,Kudoh, Kenichi,Wakamiya, Atsushi,Yamaguchi, Shigehiro
, p. 5301 - 5304 (2007/10/03)
(Chemical Equation Presented) A new intramolecular triple cyclization of bis(o-haloaryl)diacetylenes, via dilithiation followed by reaction with chalcogen elements, produces π-conjugated compounds containing heterole-1,2-dichalcogenin-heterole fused tricy
Bis(benzothieno)dithiine, a Valence Isomer of "Dithioxo-thioindigo"
Schroth, Werner,Hintzche, Ekkehard,Viola, Horst,Winkler, Ralf,Klose, Heike,et al.
, p. 401 - 408 (2007/10/02)
3-Mercaptobenzothiophene (1) is transformed with assistance of bases, especially of amines, into the benzothieno-annellated 1,2-dithiine 6 and not into the originally claimed "Dithioxo-thioindigo" trans-3.Primarily, the formation of 6 from 1 involves oxidation to the disulfide 4 which may also be used separately.Conceivable rationalizations are discussed.The same compound is accessible (in lower yield) by thionation of thioindigo with the aid of the Lawesson reagent.X-ray elucidation of 6 reveals a non-planar structure of the cyclic disulfide with a dihedral C-S-S-C-angle of 53 deg.Despite of the absence of any established chromophoric moiety, 6 is deeply red in the crystal and in solution, as it is representative for the "undisturbed" 1,2-dithiine system.Contrary to the usual behaviour of the non-annellated 1,2-dithiines, 6 displays no spontaneous sulfur extrusion under mild conditions, but only at high temperatures and in the presence of sulfur-binding agents, leading to the benzothieno-annellated thiophene 22.Moreover, 6 may be reduced to the dithiol 14 (or 13, respectively) and regenerated exclusively from this by oxidation.Further characteristic reactions of 6 are described (e.g. to the sulfoxide 18, to the pyridazine 19, and to the thiophosphoric ester 21). - Key Words: 1,2-Dithiines / Thioindigo / Thioketones / Disulphides, cyclic, molecular structure and reactions / Valence isomerization, electrocyclic / Thiophenes, derivatives of
