25796-77-4

Usage

Uses

suzuki reaction

Synthetic route

bis(2-iodo-3-thienyl)methanone (474416-61-0) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
With copper In N,N-dimethyl-formamide Reflux;	99%
With copper In N,N-dimethyl-formamide for 15h; Ullmann reaction; Reflux;	95%
With copper In N,N-dimethyl-formamide for 15h; Ullmann coupling reaction; Heating;	90%

2,6-bis(trimethylsilyl)-4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one (1187970-48-4) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
With trifluoroacetic acid In chloroform at 20℃; for 1h;	95%

spiro[4H-cyclopenta[2,1-b;3,4-b']-dithiophene-4,2'-[1,3]dioxolan] (156547-71-6) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
With hydrogenchloride Hydrolysis;	91%

3,3'dibromo-2,2'-bithiophene (51751-44-1) + N,N-Dimethylcarbamoyl chloride (79-44-7) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
Stage #1: 3,3'dibromo-2,2'-bithiophene With n-butyllithium In diethyl ether; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: N,N-Dimethylcarbamoyl chloride In diethyl ether; hexane at -78 - 20℃; Inert atmosphere;	79%
Stage #1: 3,3'dibromo-2,2'-bithiophene With n-butyllithium In diethyl ether at -78℃; for 1h; Inert atmosphere; Stage #2: N,N-Dimethylcarbamoyl chloride In diethyl ether at -78 - 20℃; Inert atmosphere;	76%
Stage #1: 3,3'dibromo-2,2'-bithiophene With n-butyllithium In diethyl ether; hexane at -70℃; for 1h; Inert atmosphere; Stage #2: N,N-Dimethylcarbamoyl chloride In diethyl ether; hexane for 3h; Inert atmosphere;	75.1%
Stage #1: 3,3'dibromo-2,2'-bithiophene With n-butyllithium In diethyl ether at -78℃; for 2h; Stage #2: N,N-Dimethylcarbamoyl chloride In diethyl ether at 20℃;	68%
Stage #1: 3,3'dibromo-2,2'-bithiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: N,N-Dimethylcarbamoyl chloride In tetrahydrofuran; hexane at -78 - 0℃; for 3h; Schlenk technique; Inert atmosphere;	58%

2,3-thiophenedicarboxylic acid anhydride (6007-83-6) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione (32281-36-0)

Conditions	Yield
at 500℃; under 1 - 5 Torr;	A 1.2% B n/a

3-thiophene carboxaldehyde (498-62-4) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / PCC / CH2Cl2 / 12 h / 20 °C 2: 90 percent / Cu / dimethylformamide / 15 h / Heating View Scheme
Multi-step reaction with 4 steps 1.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 1.2: -78 - 20 °C 2.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 2.2: -78 - 20 °C 3.1: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C 4.1: copper / N,N-dimethyl-formamide / 15 h / Reflux View Scheme
Multi-step reaction with 4 steps 1.1: n-butyllithium / diethyl ether / -78 °C 1.2: -78 - 20 °C 2.1: n-butyllithium / diethyl ether / -23 - 20 °C 2.2: -23 - 20 °C 3.1: pyridinium chlorochromate / 1,2-dichloro-ethane / 80 °C 4.1: copper / N,N-dimethyl-formamide / Reflux View Scheme

bis(2-iodothiophen-3-yl)methanol (474416-59-6) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / PCC / CH2Cl2 / 12 h / 20 °C 2: 90 percent / Cu / dimethylformamide / 15 h / Heating View Scheme
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C 2: copper / N,N-dimethyl-formamide / 15 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / 1,2-dichloro-ethane / 80 °C 2: copper / N,N-dimethyl-formamide / Reflux View Scheme
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / dichloromethane / 10 h / 25 °C 2: copper / N,N-dimethyl-formamide / 4 h / 120 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / dichloromethane / 10 h / 25 °C 2: copper / N,N-dimethyl-formamide / 4 h / 120 °C / Inert atmosphere View Scheme

di(thiophen-3-yl)methanone (26453-81-6) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 66 percent / TMSOTf / CH2Cl2 / 3 h / 20 °C 2.1: n-BuLi; I2 2.2: 90 percent / Cu / dimethylformamide / 15 h / Heating 3.1: 91 percent / aq. HCl View Scheme

2,2-Di(3-thienyl)-1,3-dioxolane (19690-72-3) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-BuLi; I2 1.2: 90 percent / Cu / dimethylformamide / 15 h / Heating 2.1: 91 percent / aq. HCl View Scheme

thiophene-2,3-dicarboxylic acid (1451-95-2) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 99.7 percent / acetic anhydride / 2 h / Heating 2: 1.2 percent / 500 °C / 1 - 5 Torr View Scheme

1,1-di(thien-3-yl)-methanol (31936-92-2) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 1.2: -78 - 20 °C 2.1: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C 3.1: copper / N,N-dimethyl-formamide / 15 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: n-butyllithium / diethyl ether / -23 - 20 °C 1.2: -23 - 20 °C 2.1: pyridinium chlorochromate / 1,2-dichloro-ethane / 80 °C 3.1: copper / N,N-dimethyl-formamide / Reflux View Scheme

3-bromo-[2,2’]bithiophenyl (19690-69-8) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: acetic acid; N-Bromosuccinimide / chloroform / 20 h / 20 - 50 °C 2.1: n-butyllithium / diethyl ether / Inert atmosphere 2.2: Inert atmosphere 3.1: n-butyllithium / hexane; tetrahydrofuran / -60 - -30 °C / Inert atmosphere 3.2: -30 - 0 °C / Inert atmosphere 4.1: trifluoroacetic acid / chloroform / 1 h / 20 °C View Scheme

3,3'-dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene (207742-50-5) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / -60 - -30 °C / Inert atmosphere 1.2: -30 - 0 °C / Inert atmosphere 2.1: trifluoroacetic acid / chloroform / 1 h / 20 °C View Scheme

3,3',5,5'-tetrabromo-2,2'-bithiophene (125143-53-5) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: n-butyllithium / diethyl ether / Inert atmosphere 1.2: Inert atmosphere 2.1: n-butyllithium / hexane; tetrahydrofuran / -60 - -30 °C / Inert atmosphere 2.2: -30 - 0 °C / Inert atmosphere 3.1: trifluoroacetic acid / chloroform / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: zinc; acetic acid; hydrogenchloride / ethanol; water / 3 h / 70 °C / Inert atmosphere 2.1: n-butyllithium / diethyl ether; hexane / 1 h / -70 °C / Inert atmosphere 2.2: 3 h / Inert atmosphere View Scheme

[2,2'-bithiophene]-3-carboxylic acid (19783-52-9) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / 12 h / 20 °C / Reflux 2: aluminum (III) chloride / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere View Scheme
Stage #1: [2,2'-bithiophene]-3-carboxylic acid With thionyl chloride In N,N-dimethyl-formamide for 12h; Reflux; Stage #2: With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 9h;	20.7 mg

3-Thiophene carboxylic acid (88-13-1) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; dipotassium hydrogenphosphate; silver(l) oxide / tert-butyl alcohol / 24 h / 130 °C / Schlenk technique; Inert atmosphere 2: thionyl chloride; N,N-dimethyl-formamide / 12 h / 20 °C / Reflux 3: aluminum (III) chloride / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: dipotassium hydrogenphosphate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(l) oxide / tert-butyl alcohol / 24 h / 20 - 130 °C / Inert atmosphere 2.1: thionyl chloride / N,N-dimethyl-formamide / 12 h / Reflux 2.2: 9 h / 0 - 20 °C View Scheme

C9H5ClOS2 → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;	20.5 mg

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + dimethyl 4,5-bis(methylthio)-1,3-dithiole phosphonate ester (138519-02-5) → 4-(4,5-Bis-methylsulfanyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene (143736-76-9)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	98%
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 15 min; 2.) 20 min;	98%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + S,S'-(2-(dimethoxyphosphoryl)-1,3-dithiole-4,5-diyl)dihexanethiol → 4-(4,5-Bis-hexylsulfanyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene (143736-84-9)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	96%
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 15 min; 2.) 20 min;	96%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) → 2,6-dibromo-4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one

Conditions	Yield
With N-Bromosuccinimide; acetic acid at 20℃;	96%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 25℃;	94%
With bromine In dichloromethane at 20℃; for 2h; Inert atmosphere;	87.1%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 0.166667h;
With N-Bromosuccinimide In tetrahydrofuran at 0℃; for 2.25h; Inert atmosphere;	17.3 g

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + malononitrile (109-77-3) → 4-dicyanomethylene-4H-cyclopenta<2,1-b;3,4-b'>dithiophene (138050-21-2)

Conditions	Yield
With piperidine	93%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + 2-(dimethoxyphosphoryl)-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester (148192-05-6) → 2-Cyclopenta[2,1-b;3,4-b']dithiophen-4-ylidene-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester (143736-80-5)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 15 min; 2.) 20 min;	91%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one-2-carbaldehyde (1376711-77-1)

Conditions	Yield
With trichlorophosphate In 1,2-dichloro-ethane at 0 - 80℃; for 6h;	91%
With trichlorophosphate In dichloromethane at 0 - 80℃; for 6h;	91%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + dimethyl 1,3-benzodithiol-2-ylphosphonate (62217-35-0) → 4-Benzo[1,3]dithiol-2-ylidene-4H-cyclopenta[2,1-b;3,4-b']dithiophene (143736-74-7)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	89%
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 15 min; 2.) 20 min;	89%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) → 4H-cyclopenta[2,1-b;3,4-b']dithiophene (389-58-2)

Conditions	Yield
With hydrazine hydrate; potassium hydroxide In ethylene glycol at 180℃;	89%
With hydrazine hydrate; potassium hydroxide In ethylene glycol at 200℃; for 2h; Inert atmosphere;	67%
With potassium hydroxide; hydrazine In ethylene glycol at 190℃; for 13h;	66%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + ethane-1,2-dithiol (540-63-6) → C11H8S4 (164727-17-7)

Conditions	Yield
With aluminium trichloride In 1,2-dichloro-ethane at 20℃; for 1h;	89%
With aluminum (III) chloride In 1,2-dichloro-ethane at 20℃;
With aluminum (III) chloride In chloroform at 25℃; Inert atmosphere;

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + 3-bromo-[2,2’]bithiophenyl (19690-69-8) → 4-(2,2’-bithiophen-3-yl)-4-hydroxycyclopenta[2,1-b;3,4-b’]dithiophene (1500083-89-5)

Conditions	Yield
Stage #1: 3-bromo-[2,2’]bithiophenyl With n-butyllithium In diethyl ether; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one In diethyl ether; hexane at -78 - 20℃; for 6h; Inert atmosphere;	88%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) → 2,6-di-iodo-cyclopenta[1,t2-b:5,4-b’]dithiophen-4-one (1222450-34-1)

Conditions	Yield
With N-iodo-succinimide; trifluoroacetic acid In acetonitrile at 20℃;	88%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + 1-bromo-4-octyloxybenzene (96693-05-9) → 4-(4-(octyloxy)phenyl)-4H-cyclopenta[1,2-B:5,4-B']dithiophen-4-ol

Conditions	Yield
With magnesium In tetrahydrofuran at 50℃; for 18h; Inert atmosphere;	85%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + 2-Bromobiphenyl (2052-07-5) → 4-(Biphenyl-2-yl)-4-hydroxy-4H-cyclopenta[2,1-b:3,4-b']dithiophene (350031-83-3)

Conditions	Yield
Stage #1: 2-Bromobiphenyl With n-butyllithium In hexane for 1h; Heating; Stage #2: 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one In tetrahydrofuran; hexane at -70℃; for 1h; Further stages.;	83%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) → C9H3BrOS2

Conditions	Yield
With bromine In dichloromethane at 20℃; for 2h; Inert atmosphere;	82.9%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + 10-(dicyanomethylidene)-9(10H)-anthrone hydrazone (156755-16-7) → 2-[10-(cyclopenta[2,1-b;3,4-b']dithiophen-4-ylidene-hydrazono)-10H-anthracen-9-ylidene]-malononitrile

Conditions	Yield
With pyridinium p-toluenesulfonate acidic;	80%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + (2-ethylhexyl)triphenylphosphonium bromide → 4-(2′-ethylhexylidene)-4H-cyclopenta[2,1-b:3,4-b′]-dithiophene (1523510-31-7)

Conditions	Yield
Stage #1: (2-ethylhexyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -82℃; Inert atmosphere; Stage #2: 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one In tetrahydrofuran; hexane at -82℃; for 0.5h;	79%
Stage #1: (2-ethylhexyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one In tetrahydrofuran; diethyl ether at -78 - 20℃; Inert atmosphere;	77%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + dimethyl [4,5-bis(butylthio)-1,3-dithiol-2-yl]phosphonate → 4-(4,5-Bis-butylsulfanyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene (143736-82-7)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	78%
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 15 min; 2.) 20 min;	78%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + 10-hydrazono-9,10-dihydroanthracen-9-one (3166-13-0) → 10-(cyclopenta[2,1-b;3,4-b']dithiophen-4-ylidene-hydrazono)-10H-anthracen-9-one

Conditions	Yield
With pyridinium p-toluenesulfonate	76%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + benzyl bromide (100-39-0) → C16H10S2

Conditions	Yield
Stage #1: benzyl bromide With triphenylphosphine Stage #2: 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one With sodium ethanolate Wittig Olefination;	76%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + n-octyltriphenylphosphoniumbromide (42036-78-2) → 4-(octylidene)-4H-cyclopenta[2,1-b:3,4-b′]dithiophene (1523510-28-2)

Conditions	Yield
Stage #1: n-octyltriphenylphosphoniumbromide With n-butyllithium In tetrahydrofuran; hexane at -82℃; Inert atmosphere; Stage #2: 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one In tetrahydrofuran; hexane at -82℃; for 0.5h;	74%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + 2-dimethoxyphosphinyl-4,5-dimethyl-1,3-dithiole (69212-98-2) → 4-(4,5-Dimethyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene (143736-78-1)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	71%
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 15 min; 2.) 20 min;	71%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + 1-bromo-4-octylbenzene (51554-93-9) → 4-(4-octylphenyl)-4H-cyclopenta[1,2-B:5,4-B']dithiophen-4-ol

Conditions	Yield
With magnesium In tetrahydrofuran at 50℃; for 18h; Inert atmosphere;	70%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) → cyclopenta[2,1-b;3,4-b']dithiophen-4-ylidene-hydrazine

Conditions	Yield
With pyridinium p-toluenesulfonate; hydrazine	68%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + dimethyl (1,3-dithiol-2-yl)phosphonate (133113-76-5) → 4-(1,3-Dithiol-2-ylidene)-4H-cyclopenta<2,1-b;3,4-b'>dithiophene (143693-14-5)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	65%
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 15 min; 2.) 20 min;	65%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) + dimethyl 4,5-bis(decylthio)-2H-1,3-dithiol-2-ylphosphonate (155442-43-6) → 4-(4,5-Bis-decylsulfanyl-[1,3]dithiol-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b']dithiophene (143736-86-1)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	64%
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 15 min; 2.) 20 min;	64%

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one (25796-77-4) → 2,3,5,6-tetrabromo-4H-cyclopenta[2,1-b:3,4-b’]dithiophen-4-one

Conditions	Yield
With bromine In chloroform at 70℃; for 12h;	63%
With bromine In chloroform for 12h; Reflux;	63%

Upstream product

• 6007-83-6 2,3-thiophenedicarboxylic acid anhydride 
• 156547-71-6 spiro[4H-cyclopenta[2,1-b;3,4-b']-dithiophene-4,2'-[1,3]dioxolan] 
• 474416-61-0 bis(2-iodo-3-thienyl)methanone 
• 498-62-4 3-thiophene carboxaldehyde 
• 26453-81-6 di(thiophen-3-yl)methanone 
• 1451-95-2 thiophene-2,3-dicarboxylic acid 
• 19690-69-8 3-bromo-[2,2’]bithiophenyl 
• 207742-50-5 3,3'-dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene 
• 125143-53-5 3,3',5,5'-tetrabromo-2,2'-bithiophene 
• 1187970-48-4 2,6-bis(trimethylsilyl)-4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one 
• 19783-52-9 [2,2'-bithiophene]-3-carboxylic acid 
• 88-13-1 3-Thiophene carboxylic acid 
• 51751-44-1 3,3'dibromo-2,2'-bithiophene 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 

Downstream Products

• 350031-83-3 4-(Biphenyl-2-yl)-4-hydroxy-4H-cyclopenta[2,1-b:3,4-b']dithiophene 
• 389-58-2 4H-cyclopenta[2,1-b;3,4-b']dithiophene 
• 365547-21-3 2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene 
• 1295502-12-3 5H-dithieno[3,2-b:2',3'-d]pyran-5-one 
• 1295502-20-3 5-(3,7-dimethyloctyl)-5-(3-methyloctyl)-5Hdithieno[3,2-b:2',3'-d]pyran 
• 942398-52-9 C₉H₃BrOS₂ 
• 1221821-39-1 6-bromo-4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene-2-carbaldehyde 
• 1315276-46-0 6-[4-(diphenylamino)phenyl]-4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene-2-carbaldehyde 
• 1416261-35-2 C₂₁H₂₀F₅NS₂Sn₂ 

Relevant academic research and scientific papers

A new, improved and convenient synthesis of 4H-cyclopenta[2,1-b:3,4-b′]-dithiophen-4-one

A new and efficient three-step synthesis of 4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one (CDT) (1) is described. This was achieved by a one-pot, regiospecific synthesis of bis(2-iodo-3-thienyl)methanol (13), its subsequent oxidation to the bls(2-iodo-3-thienyl) ketone (14) which after Ullmann coupling yielded the title compound 1.

Organic light-emitting material with thermally induced delayed fluorescence performance as well as preparation method and application thereof

The invention discloses an organic light-emitting material with thermally induced delayed fluorescence performance as well as a preparation method and application of the organic light-emitting material, belonging to the technical field of organic light-emitting materials. The organic light-emitting material takes cyclofluorenone dithiophene as a skeleton, and a bipolar organic small molecular light-emitting material is formed by connecting different donor units and receptor units. The organic light-emitting material with the thermally induced delayed fluorescence performance in the invention is of a D-A type structure (Donor-Acceptor type) containing a cyclofluorenone dithiophene unit, has good hole/electron transport property and high fluorescence quantum yield, and can be widely appliedto the fields of organic light-emitting devices, counterfeiting prevention, chemical and biological detection, biological imaging and the like; and a cyclofluorenone dithiophene intermediate preparedin the invention has good solubility in an organic phase, can be used for evaporation devices, and is also suitable for spin-coating devices.

COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME

The present specification relates to a compound and an organic light emitting device comprising the same. The compound is represented by chemical formula 1. The abovementioned compound can be used as a material for an organic material layer of an organic light emitting device. The compound according to at least one embodiment of the present invention can improve the efficiency, the low driving voltage and/or the lifetime characteristics in the organic light emitting device.COPYRIGHT KIPO 2018

An effective strategy to enhance the dielectric constant of organic semiconductors-CPDTTPD-based low bandgap polymers bearing oligo(ethylene glycol) side chains

Conjugated polymers applied in organic electronics (notably photovoltaics and photodetectors) generally exhibit relatively low dielectric constants (?r 3-4), which leads to significant recombination losses of photogenerated excitons. As a direct consequence, the performance of the resulting devices is inherently restricted. Some efforts have been directed toward increasing ?r of the photoactive organic compounds, but the general knowledge on the impact of specific structural variations on the dielectric constant and the final device output remains rather limited. In this study, this problem is addressed. A series of push-pull type alternating copolymers is synthesized based on 4H-cyclopenta[2,1-b:3,4-b′]dithiophene (CPDT) and 4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (TPD) subunits, with the aim to increase the dielectric constant using oligo(ethylene glycol) side chains. The amount of glycol substituents on the polymer backbone is gradually raised to systematically investigate its influence on the dielectric properties. Impedance measurements reveal a doubling of the dielectric constant (up to ?r 6.3) with respect to the reference polymer. Upon applying these materials in bulk heterojunction polymer solar cells, an efficiency of 4.4% is obtained for the best-performing device, with a particularly higher short-circuit current and improved fill factor compared to the pristine alkyl-substituted polymer. Importantly, a non-halogenated solvent-beneficial toward 'green' processing-can also be applied for the active layer deposition, affording comparable results.

A two-thieno cyclopentanone compound and its preparation method and application (by machine translation)

The present invention discloses a two-thieno cyclopentanone compound and its preparation method and application, which belongs to the technical field of solar cell. Said two thiophene and cyclopentanone compound, the structure of the formula I as shown: Wherein L1 , L2 Respectively and independently represent a hydrogen atom or R, and L1 , L2 At least one is a R. The invention also discloses the above-mentioned two thiophene and cyclopentanone compound of preparation method and application. The compounds of this invention introduced two fragrant amines group is branched, can make the molecule has space three-dimensional structure, to avoid material crystallization; introduced two thiophene and cyclopentanone can greatly improve the thermal stability of the material. (by machine translation)

Molecular engineering of face-on oriented dopant-free hole transporting material for perovskite solar cells with 19% PCE

Through judicious molecular engineering, novel dopant-free star-shaped D-π-A type hole transporting materials coded KR355, KR321, and KR353 were systematically designed, synthesized and characterized. KR321 has been revealed to form a particular face-on organization on perovskite films favoring vertical charge carrier transport and for the first time, we show that this particular molecular stacking feature resulted in a power conversion efficiency over 19% in combination with mixed-perovskite (FAPbI3)0.85(MAPbBr3)0.15. The obtained 19% efficiency using a pristine hole transporting layer without any chemical additives or doping is the highest, establishing that the molecular engineering of a planar donor core, π-spacer and periphery acceptor leads to high mobility, and the design provides useful insight into the synthesis of next-generation HTMs for perovskite solar cells and optoelectronic applications.

Ligand Engineering for the Efficient Dye-Sensitized Solar Cells with Ruthenium Sensitizers and Cobalt Electrolytes

Over the past 20 years, ruthenium(II)-based dyes have played a pivotal role in turning dye-sensitized solar cells (DSCs) into a mature technology for the third generation of photovoltaics. However, the classic I3-/I- redox couple limits the performance and application of this technique. Simply replacing the iodine-based redox couple by new types like cobalt(3+/2+) complexes was not successful because of the poor compatibility between the ruthenium(II) sensitizer and the cobalt redox species. To address this problem and achieve higher power conversion efficiencies (PCEs), we introduce here six new cyclometalated ruthenium(II)-based dyes developed through ligand engineering. We tested DSCs employing these ruthenium(II) complexes and achieved PCEs of up to 9.4% using cobalt(3+/2+)-based electrolytes, which is the record efficiency to date featuring a ruthenium-based dye. In view of the complicated liquid DSC system, the disagreement found between different characterizations enlightens us about the importance of the sensitizer loading on TiO2, which is a subtle but equally important factor in the electronic properties of the sensitizers.

C-H/C-H rhodium catalysis -based high-efficiency oxidation coupling reaction of preparing double-hetero aromatic ring and pyronone/cyclopentanone derivatives method

The invention relates to a method for efficiently preparing a di(hetero)arylbenzopyrone/cyclopentanone derivative through a rhodium catalysis-based C-H/C-H oxidation coupling reaction. The method comprises the following steps: 1, carrying out direct cross coupling on the C-H bond at the ortho position of the carboxyl group of a raw material (hetero)aryl carboxylic acid derivative and the C-H bond of a heteroarene derivative under the catalysis of rhodium to obtain an intermediate (orthoheteroaryl(hetero) aryl carboxylic acid derivative); and 2, carrying out an intramolecular acylation or esterification reaction to obtain the (hetero) arylbenzopyrone/cyclopentanone derivative. Compared with traditional methods, the preparation method provided by the invention has the advantages of concise synthesis steps, mild conditions, high synthesis yield, and cheap and easily available raw materials.

POLYMER COMPOUND

The invention relates to a polymer compound. A photoelectric conversion device that contains the polymer compound having a structural unit represented by formula (1) has high photoelectric conversion efficiency. (wherein, X1 and X2 are the same or different and represent a nitrogen atom or -CH-. Y1 represents a sulfur atom, an oxygen atom, a selenium atom, -N(R1)- or -CR2-CR3-. R1, R2 and R3 are the same or different and represent a hydrogen atom or a substituent. W1 represents a cyano group, a monovalent organic group having a fluorine atom or a halogen atom. W2 represents a cyano group, a monovalent organic group having a fluorine atom, a halogen atom or a hydrogen atom.

Compound used for forming high-molecular compound

The present invention provides a macromolecular compound by which the short-circuit current density and the photoelectric conversion efficiency are enhanced when the macromolecular compound is used in an organic layer contained in a photovoltaic cell. Specifically, the present invention provides a macromolecular compound having a structural unit represented by Formula (5): wherein R52 and R53 are the same as or different from each other and represent hydrogen atoms, halogen atoms, alkyl groups, alkyl oxygen radicals, alkyl sulfonium, aryl groups, aryl oxygen radicals, aryl sulfonium, aryl alkyl, aryl alkyl oxygen radicals, acyl groups, acyloxy, acylamino, imide groups, amidogen, substituted amino, substituted silicyl, substituted silicon alkyl oxygen radicals, substituted silicon alkyl harvard, silicon alkyl amine, univalent heterocyclic radical, heterocyclic oxygen radicals, heterocyclic sulfonium, aryl alkenyl, aryl alkynyl, carboxyl or cyan; W1 and W2 are the same as or different from each other and represent hydrogen atoms, halogen atoms, alkyl sulfonate base, aryl sulfonic acid ester base, aryl alkyl sulfonate base, boric acid ester residues, matte methyl, scales base, Phosphonic acid ester methyl, single halogenated methyl, boric acid residues, formyl groups, vinyl or organic tin residues.