基于萘[1,2-c:5,6-c]二[1,2,5]噻二唑共轭聚合物的高效光探测器

利用基于萘[1,2-c:5,6-c]二[1,2,5]噻二唑共轭聚合物(NTOD)为给体, 富勒烯衍生物PC71BM为受体, 制备本体异质结聚合物光探测器. NTOD与PC71BM 的共混薄膜吸收范围为300 ~ 830 nm. 通过 对NTOD:PC71BM活性层厚度的调控实现器件暗电流密度的显著降低,增强了探测器的二极管性能,同时保持较高的外量子转化效率. 当活性层厚度为385 nm时,聚合物光探测器在?0.1 V偏压下的暗电流为6.69 × 10–10 A cm?2. 在–0.1 V偏压下器件在440 ~ 800 nm的工作波段的比探测率均超过1013 cm Hz1/2 W?1,处于750 nm的工作波长下达到最大比探测率为1.50 × 1013 cm Hz1/2 W?1,光响应率为0.22 A W?1,这些结果表明基于NTOD:PC71BM的有机光探测器具有广阔的应用前景.     

New Approach to Synthesis of Tetrahydroisoquino[2,1-c] [1,3]benzodiazepine

A concise and efficient synthesis of the new compounds tetrahydroisoquino [2,1-c] [1,3]benzodiazepine 5 and 7 is reported.     

Theophylline as a new and green catalyst for the one-pot synthesis of spiro[benzo[α]pyrano[2,3-c]phenazine]and benzo[α]pyrano[2,3-c]phenazine derivatives under solvent-free conditions

A green,convenient,high yielding and one-pot procedure for the synthesis of novel spiro[benzo[α]pyrano[2,3-c]phenazine]derivatives by domino multi-component condensation reaction between 2-hydroxynaphthalene-l,4-dione,benzene-l,2-diamines,ninhydrine,and malononitrile in the presence of a catalytic amount of 1,3-dimethyl-7H-purine-2,6-dione(theophylline) as an expedient,eco-friendly and reusable solid base catalyst under thermal,microwave irradiation and solvent-free conditions.This procedure has also been applied successfully for the synthesis of benzo[α]pyrano[2,3-c]phenazines.     

New Synthetic Method of Azuleno[1,2-c]thiophenes

On the viewpoints of physical and chemical properties and biological activities, syntheses of a variety of heterocycle-fused azulenes have been repoted.[1] Of them, thiophene-fused azulenes were prepared by using different types of stating materials as follows. Azuleno[2,1-b] thiophenes are readily obtained from the reactions of 2-chloroazulene derivatives with ethyl mercaptoacetate in a few steps in good yield by Matsui[2] and Yamane.[3] On the other hand, the first synthesis of azuleno[1,2-c]thiophenes was accomplished by the reaction of 3-methoxycarbonyl-2H-cyclohepta[b]furan2-one with morpholino enamine of 3-oxotetrahydro-thiophene followed by dehydrogenation in poor yield by Fujimori.     

DABCO-催化合成呋喃并[3,2-c]香豆素类化合物

在1,4-二氮杂二环[2,2,2]辛烷(DABCO)作用下,以水为反应介质,通过3-溴乙酰基-4-羟基香豆素与芳香醛的亲核取代、分子内环化及消除的串联反应,有效合成了新型呋喃并[3,2-c]香豆素类化合物。产物结构经熔点、红外光谱、核磁共振谱等予以确认。     

新型1H-[1,2,3]三氮唑并[4,5-c]哒嗪类化合物的合成

以3,4,6-三氯哒嗪和4-碘吡唑为起始原料,分别与芳胺、碘甲烷、N-Boc哌啶-4-甲磺酸酯和2-(2-溴乙氧基)四氢-2H-吡喃通过取代、氧化和Suzuki等反应,合成了16个新型的1-H-[1,2,3]三氮唑并[4,5-c]哒嗪类化合物,其结构经1H NMR和ESI-MS表征。     

Synthesis of Furano[3,2-c]- and Pyrano[3,2-c]quinolines upon Imino Diels-Alder Reactions Initiated by Nitrosonium （NO^＋）

Efficient nitrosonium （NO＋）-initiated aza-Diels-Alder reactions of N-arylimines with 2,3-dihydrofuran or 3,4-dihydro-2H-pyran allowed access to furano[3,2-c]- or pyrano[3,2-c]quinolines. A mixture of cis and trans-quinoline isomers was obtained in various ratios and yields.     

Synthesis,photophysical and antioxidant properties of pyrrolo[3,2-c]carbazole and dipyrrolo[3,2-c:2′,3′-g]carbazole compounds

Research on Chemical Intermediates - The synthesis of (6-ethyl-1,6-dihydropyrrolo[3,2-c]carbazol-2-yl)methanol 5 and...     

One-pot synthesis of highly functionalized pyrano[2,3-c]pyrazole-4,4′-diacetate and 6-oxo-pyrano[2,3-c]pyrazole derivatives catalyzed by urea

A facile one-pot, multicomponent protocol for the synthesis of 1,4-dihydro-pyrano[2,3-c]pyrazole derivatives using a urea catalyst is reported. This transformation proceeds via a four-component reaction of ethyl acetoacetate, a hydrazine, 3-oxo-pentanedioic acid dimethyl ester, and malononitrile. The bifunctional nature of urea means that it catalyzes many steps in this transformation, including domino Knoevenagel condensation, Michael addition, and ring opening and closing reactions. This synthetic method has several advantages, including good yield, simple work-up, harmless by-products, and simple purification.     

Synthesis of Novel 5H-1,2,4-Triazolo[5′,1′:2,3] [1,3]Thiazino[5,6-c]Quinoline-5-Ones

4-chloroquinoline-3-carboxylates 2 and 5-mercapto-1,2,4-triazoles 3 have been cyclised to a novel heterocyclic system 4 .     

Pyridazines,LIV: On the synthesis of pyridazine-fused S-heterocycles: Thieno[2,3-c]pyridazine,pyrimido[4′,5′:4,5]thieno[2,3-c]pyridazine,and pyridazino[3,4-b][1,4]benzothiazine

Summary Starting from 3-chloro-4-pyridazinecarbonitrile (1), the thienopyridazine derivatives2 and3 were prepared. Condensation of3 with triethyl orthoformate afforded the novel tricyclic system4. Reaction of1 with 2-aminothiophenol, followed by treatment with NaH/DMSO was found to give the diaza-phenothiazine6 instead of the expected condensed thiazepine.Dedicated with best wishes to Prof. Dr. G. Zigeuner on the occasion of his 70^th anniversary     

Intramolecular Ullmann-type C−N coupling for the synthesis of substituted benzo[4,5]imidazo[1,2-a]pyrrolo[3,4-c]pyridines

An efficient CuI catalyzed intramolecular Ullmann-type C−N coupling reaction is described here. Newly substituted 1H-benzo[4,5]imidazo[1,2-a]pyrrolo[3,4-c]pyridine-1,3,5(2H, 11H)-trione has been easily synthesized from ortho halogenated N-substituted pyrrolo[3,4-c]pyridine-1,3,6(5H)-triones in presence of CuI catalyst and K₂CO₃ base without any ligand. This procedure is based on intramolecular Ullmann-type reaction and provides a proficient method of making fused tetracyclic heterocycles.     

Cu催化新型苯并[e]吡唑并[1,5-c][1,3]噻嗪类化合物的合成

基于底物设计的概念,建立了一种以1-(2-溴芳基)-3-乙氧基-3-(取代胺基)-2-丙烯-1-酮(1)为原料,经由5-(2-溴芳基)-3-取代胺基-1H-吡唑(2)和异硫氰酸酯(3)在溴化亚铜/邻菲罗啉催化下高化学选择性地合成苯并[e]吡唑并[1,5-c][1,3]噻嗪类衍生物的新方法.该方法操作简单、反应条件温和且收率高.     

Synthesis of two-dimensional π-conjugated polymers pendent with benzothiadiazole and naphtho[1,2-c:5,6-c]bis[1,2,5]thiadiazole moieties for polymer solar cells

Four new 2D donor–acceptor conjugated polymers were designed and synthesized.These new polymers comprised fluorenealt-triphenylamine or carbazole-alt-triphenylamine as the backbones,and pendants with 2,1,3-benzothiadiazole(BT)or naphtho[1,2-c:5,6-c]bis[1,2,5]thiadiazole(NT)in a triphenylamine unit as the side groups.By changing the acceptor BT for a stronger electron-withdrawing unit of NT moiety in the side chain,the energy levels,absorption spectra,band gaps,and charge-transport abilities of the resultant polymers could be effectively tuned.Bulk heterojunction solar cells with these polymers as the electron donors and(6,6)-phenyl-C71-butyric acid methyl ester as the electron acceptor exhibited high open-circuit voltage(more than 0.8 e V).The power conversion efficiency can be improved from 1.37%to 3.52%by replacing the BT with an NT moiety,which indicates that introducing NT as the side-chain building block can be an effective strategy to construct efficient 2D conjugated polymers for PSCs.     

Synthesis of chiral pyrrolo[1,2-c]thiazoles via intramolecular dipolar cycloaddition of münchnones: an interesting rearrangement to pyrrolo[1,2-c]thiazines

Intramolecular dipolar cycloaddition of bicyclic münchnones, 5H,7H-thiazolo[3,4-c]oxazol-4-ium-1-olates, derived from cyclodehydration of 2-substituted-N-acylthiazolidine-4-carboxylic acids are reported. A range of new pyrrolo[1,2-c]thiazole derivatives (7, 14, 15, 20, 23, and 26) were obtained as single enantiomers from 2-phenylthiazolidines, 2-benzoylthiazolidines, and 2-methylthiazolidine-4-carboxylates. Pyrrolo[1,2-c][1,4]thiazine derivative 27 was also obtained from pyrrolo[1,2-c]thiazole derivative 26. The structures of methyl (2R,4R)-2-(p-methoxybenzoyl)thiazolidine-4-carboxylate (17a), methyl (2R,4R)-2-(p-methoxybenzoyl)-N-(prop-2-ynyloxyacetyl)thiazolidine- 4-carboxylate (18), and 3-oxo-4-phenyl-3,4,6,8-tetrahydro-1H-furo[3',4':2,3]pyrrolo[1,2-c][1,4]thiazine (27) were determined by X-ray crystallography. Chirooptical studies of the pyrrolo[1,2-c]thiazoles were done by confirming the absolute configuration at the chiral center C-3.     

Dipyrrolo[1,2-a; 2′,1′-c]pyrazines. 4. Aminomethylation of alkyl substituted dipyrrolo[1,2-a; 2′,1′-c]pyrazines and 5,6-dihydrodipyrrolo[1,2-a; 2′,1′-c]pyrazines

We have studied the aminomethylation reaction of alkyl substituted dipyrrolo[1,2-a; 2,1-c]pyrazines and their 5,6-dihydro analogs using different aminomethylating agents. Use of alkoxydialkylaminomethanes (aminoacetals) as Mannich reagents leads to the highest yields of the aminomethylated dipyrrolopyrazines. The compounds prepared have been studied by mass spectrometry.For Communication 3, see [1].M. V. Lomonosov State University, Moscow 119899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 949–957, July, 1998.     

Dipyrrolo[1,2-a; 2′,1′-c]pyrazines. 5. Azo coupling of dipyrrolo[1,2-a;2′,1′-c]pyrazines and 5,6-dihydrodipyrrolo[1,2-a; 2′,1′-c]pyrazines

We have synthesized a series of previously unreported azo dyes via the azo coupling of alkyl substituted dipyrrolopyrazines with aryldiazonium chloride. For this type of substrate where one or both -positions of the pyrrole rings of the molecules are not occupied by substituents, electrophilic attack was found to occur initially at carbon atom C₍₃₎.For communication 4 see [1]M. V. Lomonosov State University, Moscow 119899, Russia Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 236–240, February, 1999.     

Synthesis of derivatives of pyrido[3′,2′:4,5]furo[3,2-c]isoquinoline heterocyclic system

An approach to the synthesis of derivatives of new heterocyclic system, pyrido[3′,2′:4,5]-furo[3,2-c]isoquinoline, was suggested. A condensation reaction of substituted 3-cyanopyridin-2(1H)-ones with methyl 2-(chloromethyl)benzoate and subsequent treatment of the condensation product with potassium tert-butoxide leads to substituted pyrido[3′,2′:4,5]furo[3,2-c]-isoquinolin-5(6H)-ones. Similarly, a condensation reaction of substituted 3-cyanopyridin-2(1H)-ones with 2-(chloromethyl)benzonitrile and subsequent treatment of the condensation product with potassium tert-butoxide gives substituted 5-aminopyrido[3′,2′:4,5]furo[3,2-c]-isoquinolines.     

Diethyl oxalacetate sodium salt as a reagent to obtain functionalized spiro[indoline-3,4′-pyrano[2,3-c]pyrazoles]

An efficient one-pot procedure for the synthesis of ethyl 6′-amino-5′-cyano-2-oxo-2′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-3′-carboxylates in moderate to high yields is described.