7774-73-4Relevant academic research and scientific papers
Highly efficient near-infrared and semitransparent polymer solar cells based on an ultra-narrow bandgap nonfullerene acceptor
Chen, Juan,Li, Guangda,Zhu, Qinglian,Guo, Xia,Fan, Qunping,Ma, Wei,Zhang, Maojie
, p. 3745 - 3751 (2019)
In this work, we design and synthesize an acceptor-donor-acceptor structured non-fullerene acceptor (ACS8) with an ultra-narrow bandgap (1.3 eV). It possesses a well-ordered molecular orientation and π-π stacking, and hence exhibits a high electron mobility of 2.65 × 10-4 cm2 V-1 s-1. Polymer solar cells (PSCs) based on PTB7-Th:ACS8 (1:2, w/w) processed using toluene and 0.5% PN (1-phenylnaphthalene) treatment exhibited an optimal power conversion efficiency (PCE) of 13.2% with an open circuit voltage (Voc) of 0.75 V, a short-circuit current density (Jsc) of 25.3 mA cm-2 and a fill factor (FF) of 69.3% under the illumination of AM 1.5G, 100 mW cm-2. This PCE is among the highest values reported in the literature to date for PSCs based on ultra-narrow bandgap acceptors (Eoptg ≤ 1.3 eV). Furthermore, semitransparent devices based on PTB7-Th:ACS8 exhibit an outstanding PCE up to 11.1% with an average visible transmittance of 28.6%.
High efficiency polymer solar cells based on alkylthio substituted benzothiadiazole-quaterthiophene alternating conjugated polymers
Zhang, Zhe,Lu, Zhen,Zhang, Jicheng,Liu, Yahui,Feng, Shiyu,Wu, Liangliang,Hou, Ran,Xu, Xinjun,Bo, Zhishan
, p. 36 - 41 (2017)
We have designed and synthesized two alkylthio substituted benzothiadiazole-quaterthiophene based conjugated polymers (P1 and P2) and investigated their photovoltaic performances. Theoretical simulation has demonstrated that the introduction of alkylthio substituents can increase the planarity of the resulted conjugated polymers. The fluorinated polymer P1 possesses a deeper HOMO energy level than the non-fluorinated polymer P2 and can form well-developed fibril networks when blended with PC71BM. PSCs based on P1:PC71BM (1:1.2, by weight) gave a PCE of 7.76% with a Voc of 0.69?V, a Jsc of 16.30?mA?cm?2 and an FF of 0.69. Our results have demonstrated that alkylthiothiophene could be a useful building block for the construction of high efficiency polymer donor materials used for PSCs.
Effect of regioregularity and role of heteroatom on the chiral behavior of oligo(heteroalkyl thiophene)s
Marinelli, Martina,Angiolini, Luigi,Lanzi, Massimiliano,Di Maria, Francesca,Salatelli, Elisabetta
supporting information, p. 1361 - 1376 (2020/11/23)
Novel optically active oligothiophenes bearing electron-donating chiral side chains have been prepared by synthetic methods suitable to achieve regioregular head-to-tail and head-to-head/tail-to-tail derivatives. In particular, the chiral (S)-(2-methyl)butyl moiety was linked at position 3 of the thiophene ring through heteroatoms, such as S or O, to evaluate its effect on the macro molecular aggregation and, consequently, on the chiroptical properties of the material in the solid state. The materials have been fully characterized and investigated by optical and chiroptical methods upon aggregation both from the solution and as cast films. Compared with the related head-to-tail and head-to-head/tail-to-tail poly(3-alkyl)thiophene derivatives, with the same optically active moiety directly linked to the ring and possessing a higher polymerization degree, the chiroptical properties of the newly synthesized oligomers were significant, or even better, and provided insight into the role of intrachain–interchain interactions between the heteroatom and the thienyl sulfur atom.
A successful chemical strategy to induce oligothiophene self-assembly into fibers with tunable shape and function
Di Maria, Francesca,Olivelli, Pasquale,Gazzano, Massimo,Zanelli, Alberto,Biasiucci, Mariano,Gigli, Giuseppe,Gentili, Denis,D'Angelo, Pasquale,Cavallini, Massimiliano,Barbarella, Giovanna
supporting information; experimental part, p. 8654 - 8661 (2011/07/29)
Functional supramolecular architectures for bottom-up organic nano- and microtechnology are a high priority research topic. We discovered a new recognition algorithm, resulting from the combination of thioalkyl substituents and head-to-head regiochemistry of substitution, to induce the spontaneous self-assembly of sulfur overrich octathiophenes into supramolecular crystalline fibers combining high charge mobility and intense fluorescence. The fibers were grown on various types of surfaces either as superhelices or straight rods depending on molecular structure. Helical fibers directly grown on a field effect transistor displayed efficient charge mobility and intrinsic 'memory effect'. Despite the fact that the oligomers did not have chirality centers, one type of hand-helicity was always predominant in helical fibers, due to the interplay of molecular atropisomerism and supramolecular helicity induced by terminal substituents. Finally, we found that the new sulfur overrich oligothiophenes can easily be prepared in high yields through ultrasound and microwave assistance in green conditions.
Synthesis of two novel cysteine-functionalized thiophenes
Cagnoli, Rita,Lanzi, Massimiliano,Mucci, Adele,Parenti, Francesca,Schenetti, Luisa
, p. 267 - 271 (2007/10/03)
The synthetic approach to methyl N-(tert-butoxycarbonyl)-S-(3-thienyl)-L- cysteinate (1) and methyl N-(tert-butoxycarbonyl)-S-[2-(3-thienyl)ethyl]-L- cysteinate (2) through tosylate intermediates is reported and discussed. These compounds, which combine the properties of the cysteine side-chain with those of the thiophene ring represent both potential bioactive molecules and interesting synthons for the development of new materials.
Gas-phase reaction of 2-chlorothiophene with hydrogen sulfide in the presence of alcohols
Deryagina,Sukhomazova,Levanova
, p. 40 - 45 (2007/10/03)
The effect of methanol and ethanol on the route of the gas-phase reaction of 2-chlorothiophene with hydrogen sulfide, leading to 2-thiophenethiol and to bis(2-thienyl) sulfide, has been investigated. It was found that methanol significantly enhances this
Hypolipidaemic condensed 1,4-thiazepines
-
, (2008/06/13)
The invention provides a compound of formula (I), wherein n is an integer of from 0 to 2; R is an optional substituent; R1 is hydrogen or C1-6 alkyl; R2 is an atom or group selected from hydrogen, C1-4 alkyl (including cycloalkyl and cycloalkylalkyl), C1-4 alkoxy, pyrryl, thienyl, pyridyl, 1,3-benzodioxolo, phenyl and naphthyl, which groups are optionally substituted; R3 is hydrogen, OH, C1-6 alkyl, C1-6 alkoxy or --O C1-6 acyl; R4 is a group independently selected from C1-6 alkyl (including cycloalkyl and cycloalkylalkyl), C2-6 alkenyl, and C2-6 -alkynyl which groups are optionally substituted; R5 is a group independently selected from C2-6 alkyl (including cycloalkyl and cycloalkylalkyl), C2-6 alkenyl and C2-6 alkynyl, which groups are optionally substituted; or R4 and R5, together with the carbon atom to which they are attached, form a C3-7 spiro cycloalkyl group which is optionally substituted; R6 and R7 are independently selected from hydrogen and C1-6 alkyl; and X is an aromatic or non-aromatic monocyclic or bicyclic ring system having from 5 to 10 carbon atoms (including the two carbon atoms forming part of the thiazepine ring) wherein optionally one or more of the carbon atoms is/are replaced by heteroatom(s) independently selected from nitrogen, oxygen and sulphur, or X is an aromatic or non-aromatic monocyclic or bicyclic ring system having from 5 to 10 carbon atoms (including the two carbon atoms forming part of the thiazepine ring) wherein one or more of the carbon atoms is/are replaced by heteroatom(s) independently selected from nitrogen, oxygen and sulphur; and salts, solvates and physiologically functional derivatives thereof, pharmaceutical formulations comprising such compounds, processes for their preparation and their use in reducing bile acid uptake and hence as hypolipidaemic compounds. STR1
Formation of thiophenethiols by flash vacuum pyrolysis of 1,6,6aλ4-trithiapentalenes
Flammang, Robert,Barbieux-Flammang, Monique,Gerbaux, Pascal,Pedersen, Carl Th.
, p. 1261 - 1264 (2007/10/03)
The thermal behaviour of 1,6,6aλ4-trithiapentalene 3 and some methyl-substituted derivatives 5-7 has been investigated using a combination of flash vacuum pyrolysis (FVP), tandem mass spectrometry (MS-MS) and matrix isolation IR spectroscopy. the main products of the fragmentation (losses of CS and/or CH2=C=S) are shown to be thiophene-3-thiones (or the thiol tautomers) which are also shown to be readily available by direct sulfuration of thiophenes in chemical ionization (CS2 reagent gas) conditions.
HIGH-TEMPERATURE ORGANIC SYNTHESIS. XL. THERMAL HETEROCYCLIZATION OF BIS(3-CHLORO-2-BUTENYL) DISULFIDE
Turchaninova, L. P.,Sukhomazova, E. N.,Levanova, E. P.,Korchevin, N. A.,Deryagina, E. N.,Voronkov, M. G.
, p. 1995 - 1998 (2007/10/02)
The thermolysis of bis(3-chloro-2-butenyl) disulfide in a stream of nitrogen (350-500 deg C) leads to 3-thiophenethiol and 5-methyl-1,2-dithiole-3-thione with an overall yield of up to 45percent.The radical path for the formation of these products and, particularly, the participation of sulfhydryl radicals (HS) in the process is discussed.
THERMAL HYDROTHIOLYSIS OF DI(2-THIENYL)SULFIDE IN THE GASEOUS AND LIQUID PHASE
Voronkov, M. G.,Deryagina, E. N.,Papernaya, L. K.,Sukhomazova, E. N.,Korchevin, N. A.,Efremova, G. G.
, p. 1301 - 1306 (2007/10/02)
At 500-600 deg C, di(2-thienyl)sulfide is converted to thiophene, thiophene thiols, dithienyls, and dithienothiophenes, and isomerized to 2,3-dithienylsulfide.Hydrogen sulfide accelerates these reactions significantly.In the liquid phase the thermal conversion of di(2-thienyl)sulfide takes place only with the participation of elemental sulfur or in the system sulfur-hydrogen sulfide.Thiophene and diethienothiophenes are not formed in this case, while isomerization occurs to a large degree.The observed thermal conversions of di(2-thienyl)sulfide are based on the addition of thiyl radicals to the double bonds of the thiophene ring and to the sulfide sulfur atom.
