共查询到20条相似文献,搜索用时 46 毫秒
1.
Duryodhan SahuHarihara Padhy Dhananjaya PatraJen-Fu Yin Ying-Chan HsuJiann-T’Suen Lin Kuang-Lieh LuKung-Hwa Wei Hong-Cheu Lin 《Tetrahedron》2011,67(2):303-311
Four novel symmetrical organic dyes (S1-S4) configured with acceptor-donor-acceptor (A-D-A) structures containing electron donating fluorene (S1 and S2) and N-alkyl dithieno[3,2-b:2′,3′-d]pyrrole (DTP) (S3 and S4) cores terminated with two anchoring cyanoacrylic acids (as electron acceptors) were synthesized and applied to dye-sensitized solar cells (DSSCs). The DSSC device based on S2 dye showed the best photovoltaic performance among S1-S4 dyes: a maximum monochromatic incident photon-to-current conversion efficiency (IPCE) of 76%, a short circuit current (JSC) of 12.27 mA/cm2, an open circuit voltage (VOC) of 0.61 V, a fill factor (FF) of 0.63, and an overall power conversion efficiency (η) of 4.73%. Besides, the utilization of chenodoxycholic acid (CDCA) as a co-adsorbent in the DSSC device based on S3 dye showed a significant improvement in its η value (from 3.70% to 4.31%), which is attributed to the suppression of dye aggregation on TiO2 surface and thus to increase the JSC value eventually. 相似文献
2.
Shunsuke Hayashi Takashi Ishikawa Tatsuo Asai Colin Turnbull Kanzo Sakata Koji Ogawa 《Tetrahedron》2004,60(33):7005-7013
The hydrolysis of 2-phenylethyl β-d-glucopyranoside (3) was found to be partially inhibited by feeding with 2-phenyl-N-glucosyl-acetamidiumbromide (8), a β-glucosidase inhibitor, resulting in a decrease in the diurnal emission of 2-phenylethanol (2) from Rosa damascena Mill. flowers. Detection of [1,1,2,2′,3′,4′,5′,6′-2H8]-2 and [1,2,2′,3′,4′,5′,6′-2H7]-2 from R. ‘Hoh-Jun’ flowers fed with [1,1,2,2′,3′,4′,5′,6′-2H8]-3 suggested that β-glucosidase, alcohol dehydrogenase, and reductase might be involved in scent emission. Comprehensive GC-SIM analyses revealed that [1,2,2,2′,3′,4′,5′,6′-2H8]-2 and [1,2,2,2′,3′,4′,5′,6′-2H8]-3 must be biosynthesized from [1,2,2,2′,3′,4′,5′6′-2H8] l-phenylalanine ([2H8]-1) with a retention of the deuterium atom at α-position of [2H8]-1. 相似文献
3.
Jean M ChezalEmmanuel Moreau Olivier ChavignonClaire Lartigue Yves BlacheJean C Teulade 《Tetrahedron》2003,59(31):5869-5878
Novel dipyrido[1,2-a;3′,4′-d]imidazoles 7a-d, dipyrido[1,2-a;4′,3′-d]imidazoles 8a,c and pyrido[1′,2′;1,2]imidazo[4,5-d]pyridazine derivatives 9a-d were synthesized by two pathways: thermal electrocyclic reaction of 3-alkenylimidazopyridine-2-oximes 10 and direct condensation of ethyl glycinate (or hydrazine) with 2,3-dicarbonylimidazo[1,2-a]pyridines 11. 相似文献
4.
Shin-ichi NayaMakoto Nitta 《Tetrahedron》2003,59(21):3709-3718
Novel condensation reaction of tropone with N-substituted and N,N′-disubstitued barbituric acids in Ac2O afforded 5-(cyclohepta-2′,4′,6′-trienylidene)pyrimidine-2(1H),4(3H),6(5H)-trione derivatives (8a-f) in moderate to good yields. The 13C NMR spectral study of 8a-f revealed that the contribution of zwitterionic resonance structures is less important as compared with that of 8,8-dicyanoheptafulvene. The rotational barriers (ΔG‡) around the exocyclic double bond of mono-substituted derivatives 8a-c were obtained to be 14.51-15.03 kcal mol−1 by the variable temperature 1H NMR measurements. The electrochemical properties of 8a-f were also studied by CV measurement. Upon treatment with DDQ, 8a-c underwent oxidative cyclization to give two products, 7 and 9-substituted cyclohepta[b]pyrimido[5,4-d]furan-8(7H),10(9H)-dionylium tetrafluoroborates (11a-c·BF4− and 12a-c·BF4−) in various ratios, while that of disubstituted derivatives 8d-f afforded 7,9-disubstituted cyclohepta[b]pyrimido[5,4-d]furan-8(7H),10(9H)-dionylium tetrafluoroborate (11d-f·BF4−) in good yields. Similarly, preparation of known 5-(1′-oxocycloheptatrien-2′-yl)-pyrimidine-2(1H),4(3H),6(5H)-trione derivatives (14a-d) and novel derivatives 14e,f was carried out. Treatment of 14a-c with aq. HBF4/Ac2O afforded two kinds of novel products 11a-c·BF4− and 12a,c·BF4− in various ratios, respectively, while that of 14d-f afforded 11d-f. The product ratios of 11a-c·BF4− and 12a-c·BF4− observed in two kinds of cyclization reactions were rationalized on the basis of MO calculations of model compounds 20a and 21a. The spectroscopic and electrochemical properties of 11a-f·BF4− and 12a-c·BF4− were studied, and structural characterization of 11c·BF4− based on the X-ray crystal analysis and MO calculation was also performed. 相似文献
5.
Kathleen V Kilway Keith A Lindgren James A Watson Jr. Robert D Ingalls Robert A Pascal Jr. 《Tetrahedron》2004,60(10):2433-2438
Oxygenation of 2,5,9,12-tetra(tert-butyl)diacenaphtho[1,2-b:1′,2′-d]-thiophene (1, C40H44S) by peracids gave the cyclic sulfonic ester 4 (2,7,10,13-tetra(tert-butyl)diacenaphtho[1,2-c:1′,2′-e]oxathiin 5,5-dioxide, C40H44O3S) which, when heated in nitrobenzene, is converted into a complex, macrocyclic anhydride 3 (C80H88O3), which is derived from two molecules of 4. Further investigation found a likely intermediate in this reaction, 4,4′,7,7′-tetra(tert-butyl)-1,1′-biacenaphthylenylidene-2,2′-dione (5, C40H44O2), apparently formed from 4 by additional oxidation. Anhydride 3 plausibly arises by Diels-Alder reaction of 4 and 5 followed by several ring fragmentations. The structures of 3, 4, and 5 were unambiguously established by X-ray crystallography. 相似文献
6.
Chih-Chin Chi 《Tetrahedron》2004,60(48):10869-10876
Refluxing an o-dichlorobenzene solution of 2,5-disubstituted thienosultines 10a-f with [60]fullerene for 2-24 h gave both 1:1 and 2:1 cycloadducts in 37-79% isolated yields. The reaction was highly accelerated by microwave irradiation giving comparable yields of cycloadducts. Sultines 10a-f underwent cheletropic extrusion of SO2 to form the corresponding non-Kekulé biradical intermediates 11a-f, which were subsequently trapped by [60]fullerene to form corresponding cycloadducts. The activation energy barriers (ΔGc≠) determined for the boat-to-boat inversion of these 4′,5′,6′,7′-tetrahydrobenzo[c]thieno-[5′,6′:1,2][60]fullerene adducts 12a-f were found to be in the range of 13.5-14.8 kcal/mol. Unexpectedly, one of the monoadduct 12a was found to be labile when kept in air under ambient light. Two new products 15 (a sulfine-enone) and 16 (an endione) were isolated from the decomposed 12a and were found to derive from self-sensitized singlet oxygen reaction on the 2,5-dimethylthieno moiety of 12a. 相似文献
7.
Conceptually new, enantiomerically pure bicyclic tetrahydrofuro[1,2-a]-A-ring phosphine oxides (+)-4 and (−)-4 were successfully prepared from methyl 2-pyrone-3-carboxylate and (S)- or (R)-2-(tert-butyldimethylsilyloxy)methyl-2,3-dihydrofuran, respectively. In addition, (2′-hydroxymethyl)tetrahydrofuro[1,2-a]-25-hydroxyvitamin D33a and 3b as new A-ring-modified analogs of the natural hormone 1α,25-dihydroxyvitamin D3 were readily synthesized by using Lythgoe-type coupling of the A-ring phosphine oxides (+)-4 and (−)-4 with C,D-ring ketone (+)-5. 相似文献
8.
Chakapong Intaraudom Aibrohim DramaeSumalee Supothina Somjit KomwijitPattama Pittayakhajonwut 《Tetrahedron》2014
Eight new compounds including 9′-[2-amino-3-(4″-O-methyl-α-rhamnopyranosyloxy) phenyl]nonanoic acid (1), 9′-[2-amino-3-(4″-O-methyl-α-ribopyranosyloxy)phenyl] nonanoic acid (2), 11′-[2-amino-3-(4″-O-methyl-α-rhamnopyranosyloxy)phenyl]undecanoic acid (3), 11′-[2-amino-3-(4″-O-methyl-α-ribopyranosyloxy)phenyl]undecanoic acid (4), 8-(4′-O-methyl-α-rhamnopyranosyloxy)-3,4-dihydroquinolin-2(1H)-one (5), 8-(4′-O-methyl-α-ribopyranosyloxy)-3,4-dihydroquinolin-2(1H)-one (6), 8-(4′-O-methyl-α-rhamnopyranosyloxy)-2-methyquinoline (7), and 8-(4′-O-methyl-α-ribopyranosyloxy)-2-methylquinoline (8) were isolated from Actinomadura sp. BCC27169. The chemical structures of these compounds were determined based on NMR and high-resolution mass spectroscopy. The absolute configurations of these monosaccharides were revealed by the hydrolysis of compounds 7 and 8. Compounds 3 and 8 exhibited antitubercular activity at MIC 50 μg/mL. Only compound 3 showed cytotoxicity against KB cell at IC50 18.63 μg/mL, while other isolated compounds were inactive at tested maximum concentration (50 μg/mL). 相似文献
9.
Piotr Jaunky 《Journal of organometallic chemistry》2005,690(6):1429-1455
An efficient route to the novel tridentate phosphine ligands RP[CH2CH2CH2P(OR′)2]2 (I: R = Ph; R′ = i-Pr; II: R = Cy; R′ = i-Pr; III: R = Ph; R′ = Me and IV: R = Cy; R′ = Me) has been developed. The corresponding ruthenium and iron dicarbonyl complexes M(triphos)(CO)2 (1: M = Ru; triphos = I; 2: M = Ru; triphos = II; 3: M = Ru; triphos = III; 4: M = Ru; triphos = IV; 5: M = Fe; triphos = I; 6: M = Fe; triphos = II; 7: M = Fe; triphos = III and 8: M = Fe; triphos = IV) have been prepared and fully characterized. The structures of 1, 3 and 5 have been established by X-ray diffraction studies. The oxidative addition of MeI to 1-8 produces a mixture of the corresponding isomeric octahedral cationic complexes mer,trans-(13a-20a) and mer,cis-[M(Me)(triphos)(CO)2]I (13b-20b) (M = Ru, Fe; triphos = I-IV). The structures of 13a and 20a (as the tetraphenylborate salt (21)) have been verified by X-ray diffraction studies. The oxidative addition of other alkyl iodides (EtI, i-PrI and n-PrI) to 1-8 did not afford the corresponding alkyl metal complexes and rather the cationic octahedral iodo complexes mer,cis-[M(I)(triphos)(CO)2]I (22-29) (M = Ru, Fe; triphos = I-IV) were produced. Complexes 22-29 could also be obtained by the addition of a stoichiometric amount of I2 to 1-8. The structure of 22 has been verified by an X-ray diffraction study. Reaction of 13a/b-20a/b with CO afforded the acetyl complexes mer,trans-[M(COMe)(triphos)(CO)2]I, 30-37, respectively (M = Ru, Fe; triphos = I-IV). The ruthenium acetyl complexes 30-33 reacted slowly with 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) even in boiling acetonitrile. Under the same conditions, the deprotonation reactions of the iron acetyl complexes 34-37 were completed within 24-40 h to afford the corresponding zero valent complexes 5-8. It was not possible to observe the intermediate ketene complexes. Tracing of the released ketene was attempted by deprotonation studies on the labelled species mer,trans-[Fe(COCD3)(triphos)(CO)2]I (38) and mer,trans-[Fe(13COMe)(triphos)(CO)2]I (39). 相似文献
10.
Mariadel Déniz Jorge Pasán Oscar Fabelo Laura Cañadillas-Delgado Pablo Lorenzo-Luis Fernando Lahoz David López Consuelo Yuste Miguel Julve Catalina Ruiz-Pérez 《Comptes Rendus Chimie》2012,15(10):911-923
The synthesis, crystal structure, thermal analysis and spectroscopic studies of five zinc(II) complexes of formulae [Zn(Memal)(H2O)]n (1) and [Zn2(L)(Memal)2(H2O)2]n (2-5) [H2Memal = methylmalonic acid, and L = 4,4′-bipyridine (4,4′-bpy) (2), 1,2-bis(4-pyridyl)ethylene (bpe) (3), 1,2-bis(4-pyridyl)ethane (bpa) (4) and 4,4′-azobispyridine (azpy) (5)] are presented here. The crystal structure of 1 is a three-dimensional arrangement of zinc(II) cations interconnected by methylmalonate groups adopting the μ3-κ2O:κO’:κO”:κO”’ coordination mode to afford a rare (10,3)-d utp-network. The structures of the compounds 2-5 are also three-dimensional and they consist of corrugated square layers of methylmalonate-bridged zinc(II) ions which are pillared by bis-monodentate 4,4′-bpy (2), bpe (3), bpa (4) and azpy (5) ligands. The Memal ligand in 2-5 adopts the μ3-κO:κO′:κO′′:κO′′′ coordination mode. Each zinc(II) ion in 1-5 is six-coordinated with five (1)/four (2-5) methylmalonate-oxygen atoms, a water molecule (1-5) and a nitrogen atom from a L ligand (2-5) building distorted octahedral environments. The rod-like L co-ligands in 2-5 appear as useful tools to control the interlayer metal-metal separation, which covers the range 8.4311(5) Å (2) – 9.644(3) Å (5). The influence of the co-ligand on the fluorescence properties of this series of compounds has been analyzed and discussed by steady-state and time resolved spectroscopy on all five compounds in the solid state. 相似文献
11.
A series of salen-type zirconium complexes of the general formula LZrCl2 (L = N,N′-ethylenebis(salicylideneiminate), 3a; N,N′-ethylenebis(3,5-di-tert-butylsalicylideneiminate), 3b; N,N′-ethylenebis(5-methoxysalicylideneiminate), 3c; N,N′-ethylenebis(5-chlorosalicylideneiminate), 3d; N,N′-ethylenebis(5-nitrosalicylideneiminate), 3e; N,N′-o-phenylenebis(salicylideneiminate), 4a; N,N′-o-phenylenebis(3,5-di-tert-butylsalicylideneiminate), 4b; N,N′-o-phenylenebis(5-methoxysalicylideneiminate), 4c; N,N′-o-phenylenebis(5-chloro-salicylideneiminate), 4d) were prepared. The crystal structures of 6- and 7-coordinate zirconium complexes 4b and [4b · OCMe2] were determined by X-ray crystallography, which reveals that a salen-type zirconium complex possesses a labile coordination site on the Zr center with a relatively stable framework and that the coordination and the dissociation of O-donor molecules occur readily at this site. The catalytic properties of 3(a-e) and 4(a-d) were studied for ethylene oligomerization in combination with Et2AlCl as co-catalyst. Complex 3c featuring a methoxy-substituted salen ligand displayed higher activity than its analogous precursors having chloro and nitro groups as substituents. The catalytic reactions by 3(a-e) and 4(a-d) gave C4-C10 olefins and low-carbon linear α-olefins in good selectivity. 相似文献
12.
Naphtho[1,2-b]furans 1a-f, naphtho[2,1-b]furans 2a-f, benzo[1,2-b:5,4-b′]difurans 3a-b, benzo[1,2-b:4,5-b′]difurans 4a-b, and benzo[1,2-b:4,3-b′]difurans 5a-b were synthesized by base-catalyzed cyclization reaction of the corresponding o-alkoxybenzoylarene derivatives. The o-alkoxybenzoylarenes were obtained from the etherification reaction of the o-hydroxybenzoylarenes, which were prepared either by the reaction of methoxyarenes with benzoyl chloride in the presence of aluminum chloride or by photo-Fries rearrangement of aryl benzoates. 相似文献
13.
Mono(iminophosphorane) 4 was selectively prepared from the reaction of 3,4-diaminothieno[2,3-b]thiophene 3 with excess triphenylphosphine, C2Cl6, and Et3N due to intramolecular double hydrogen bond formation. Mono(iminophosphorane) 4 reacted with aromatic isocyanates to give stable carbodiimides 8, which were further treated with aliphatic secondary or primary amines to give 2-amino substituted thieno[3′,2′:4,5]thieno[3,2-d]pyrimidin-4(3H)-ones 10 or 12 in the presence of a catalytic amounts of EtO−Na+. However, in the presence of a catalytic amounts of potassium carbonate, the carbodiimides 8 were transformed into previously unreported 5H-2,3-dithia-5,7-diaza-cyclopenta[c,d]indenes 13 via direct cyclization in high yields. The reaction of carbodiimides 8 with phenols in the presence of a catalytic amounts of potassium carbonate gave a mixture of 2-aryloxy substituted thieno[3′,2′:4,5]thieno[3,2-d]pyrimidin-4(3H)-ones 14 and 13. X-ray structure analysis of 10m supported the structure and the proposed reactivity of amino group. 相似文献
14.
Takeshi Ohnishi 《Journal of organometallic chemistry》2008,693(2):269-277
Reactions of Mo(II)-tetraphosphine complex [MoCl2(κ4-P4)] (2; P4 = meso-o-C6H4(PPhCH2CH2PPh2)2) with a series of small molecules have been investigated. Thus, treatment of 2 with alkynes RCCR′ (R = Ph, R′ = H; R = p-tolyl, R′ = H; R = Me, R′ = Ph) in benzene or toluene gave neutral mono(alkyne) complexes [MoCl2(RCCR′)(κ3-P4)] containing tridentate P4 ligand, which were converted to cationic complexes [MoCl(RCCR′)(κ4-P4)]Cl having tetradentate P4 ligand upon dissolution into CDCl3 or CD2Cl2. The latter complexes were available directly from the reactions of 2 with the alkynes in CH2Cl2. On the other hand, treatment of 2 with 1 equiv. of XyNC (Xy = 2,6-Me2C6H3) afforded a seven-coordinate mono(isocyanide) complex [MoCl2(XyNC)(κ4-P4)] (7), which reacted further with XyNC to give a cationic bis(isocyanide) complex [MoCl(XyNC)2(κ4-P4)]Cl (8). From the reaction of 2 with CO, a mono(carbonyl) complex [MoCl2(CO)(κ4-P4)] (9) was obtained as a sole isolable product. Reaction of 9 with XyNC afforded [MoCl(CO)(XyNC)(κ4-P4)]Cl (10a) having a pentagonal-bipyramidal geometry with axial CO and XyNC ligands, whereas that of 7 with CO resulted in the formation of a mixture of 10a and its isomer 10b containing axial CO and Cl ligands. Structures of 7 and 9 as well as [MoCl(XyNC)2(κ4-P4)][PF6](8′) and [MoCl(CO)(XyNC)(κ4-P4)][PF6] (10a′) derived by the anion metathesis from 8 and 10a, respectively, were determined in detail by the X-ray crystallography. 相似文献
15.
We have accomplished efficient synthesis of planar-chiral bridged 2,2′-bipyridine (S)-6, C2-symmetric bipyridinophane (S,S)-7, bridged 2,2′:6′,2″-terpyridines (S)-11, and C2-symmetric terpyridine (S,S)-12 by metal-mediated biaryl cross-coupling or homo-coupling reactions of the corresponding 6-halo[10](2,5)pyridinophanes. Stille-type and Negishi cross-coupling reactions are particularly useful for the syntheses of 6, 11, and 12. On the other hand, nickel-mediated homo-coupling reaction worked best for achieving the synthesis of structurally unique bipyridinophane 7. 相似文献
16.
The diiron complexes [Fe(Cp)(CO){μ-η2:η2-C[N(Me)(R)]NC(C6H3R′)CCH(Tol)}Fe(Cp)(CO)] (R = Xyl, R′ = H, 3a; R = Xyl, R′ = Br, 3b; R = Xyl, R′ = OMe, 3c; R = Xyl, R′ = CO2Me, 3d; R = Xyl, R′ = CF3, 3e; R = Me, R′ = H, 3f; R = Me, R′ = CF3, 3g) are obtained in good yields from the reaction of [Fe2{μ-CN(Me)(R)}(μ-CO)(CO)(p-NCC6H4R′)(Cp)2]+ (R = Xyl, R′ = H, 2a; R = Xyl, R′ = Br, 2b; R = Xyl, R′ = OMe, 2c; R = Xyl, R′ = CO2Me, 2d; R = Xyl, R′ = CF3, 2e; R = Me, R′ = H, 2f; R = Me, R′ = CF3, 2g) with TolCCLi. The formation of 3 involves addition of the acetylide at the coordinated nitrile and C-N coupling with the bridging aminocarbyne together with orthometallation of the p-substituted aromatic ring and breaking of the Fe-Fe bond. Complexes 3a-e which contain the N(Me)(Xyl) group exist in solution as mixtures of the E-trans and Z-trans isomers, whereas the compounds 3f,g, which posses an exocyclic NMe2 group, exist only in the Z-cis form. The crystal structures of Z-trans-3b, E-trans-3c, Z-trans-3e and Z-cis-3g have been determined by X-ray diffraction experiments. 相似文献
17.
A convenient method for the preparation of benzofuro[3,2-c]isoquinoline derivatives is described. The condensation reaction of methyl 2-(chloromethyl)-benzoate with substituted salicylonitriles 7a-c and intramolecular cyclization of the resulting substituted methyl 2-[(2-cyanobenzyl)oxy]benzoates 10a-c using potassium tert-butoxide results in the substituted benzofuro[3,2-c]isoquinolin-5(6H)-ones 1a-c. The same sequence of reactions starting from 2-(chloromethyl)benzonitrile and compounds 7a-c gave substituted 5-aminobenzofuro[3,2-c]isoquinolines 13a-c. In addition, this method is useful for the synthesis of other heterocycles. For example, using 1-cyano-2-naphthol 16, instead of the salicylonitriles 7a-c, gives naphtho[1′,2′:4,5]furo[3,2-c]isoquinolines. 相似文献
18.
The addition of hydrazine to functionalized furans 2a-d leads to a variety of 4,4′-bipyrazoles 4a-c depending on the structure of the starting materials. In one example, compound 2c was first converted to an intermediate, furo[3,4-d]pyridazine 3c which was then transformed into 4,4′-bipyrazole 4c on reacting with hydrazine. 相似文献
19.
Rubén A. Machado María Cristina Goite Ysaura De Sanctis Antony J. Deeming Anibal Sierralta Teresa González 《Journal of organometallic chemistry》2007,692(4):894-902
The reaction of the labile compound [Re2(CO)8(CH3CN)2] with 2,3-bis(2-pyridyl)pyrazine in dichloromethane solution at reflux temperature afforded the structural dirhenium isomers [Re2(CO)8(C14H10N4)] (1 and 2), and the complex [Re2(CO)8(C14H10N4)Re2(CO)8] (3). In 1, the ligand is σ,σ′-N,N′-coordinated to a Re(CO)3 fragment through pyridine and pyrazine to form a five-membered chelate ring. A seven-membered ring is obtained for isomer 2 by N-coordination of the 2-pyridyl groups while the pyrazine ring remains uncoordinated. For 2, isomers 2a and 2b are found in a dynamic equilibrium ratio [2a]/[2b] = 7 in solution, detected by 1H NMR (−50 °C, CD3COCD3), coalescence being observed above room temperature. The ligand in 3 behaves as an 8e-donor bridge bonding two Re(CO)3 fragments through two (σ,σ′-N,N′) interactions. When the reaction was carried out in refluxing tetrahydrofuran, complex [Re2(CO)6(C14H10N4)2] (4) was obtained in addition to compounds 1-3. The dinuclear rhenium derivative 4 contains two units of the organic ligand σ,σ′-N,N′-coordinated in a chelate form to each rhenium core. The X-ray crystal structures for 1 and 3 are reported. 相似文献
20.
Synthesis, characterization, molecular structure, and redox properties of a new quinoidal terthiophene incorporated with a thieno[3,4-c]pyrrole moiety (5) are described. Although an electrochemical reduction of 5 formally produces the non-classical thieno[3,4-c]pyrrole moiety, 5 showed a reversible reduction wave on cyclic voltammogram, indicating that the thieno[3,4-c]pyrrole moiety can be stabilized by delocalized 10π-conjugated system in the dianion state of 5. However, the reduction potential was largely affected by incorporation of the thieno[3,4-c]pyrrole and shifted cathodically by 0.4 V compared to that of the parent quinodial terthiophene (1). 相似文献