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inquiryProduct Name: 2,5-Di(HD)-3,6-di(5-broMothiophen)diketopyrrolopyrrole Synonyms: 2,5-Di(HD)-3,6-di(5-broMothiophen)diketopyrrolopyrrole;3,6-Bis(5-broMo-2-thienyl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione;3,6-bis(5-broMo-2-thien
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3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
Conditions | Yield |
---|---|
With N-Bromosuccinimide In chloroform at 50℃; for 2h; Inert atmosphere; | 79.9% |
With N-Bromosuccinimide In chloroform for 48h; Darkness; | 61% |
With N-Bromosuccinimide In chloroform for 48h; Darkness; | 60% |
3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
A
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
B
3-(5-bromothiophen-2-yl)-2,5-bis(2-hexyldecyl)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
Conditions | Yield |
---|---|
With N-Bromosuccinimide In chloroform at 0 - 20℃; Darkness; | A 17% B 56% |
7-(iodomethyl)pentadecane
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 120 °C 2: N-Bromosuccinimide / chloroform / 20 °C View Scheme |
thiophene-2-carbonitrile
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium / tert-Amyl alcohol / 120 °C 2: potassium carbonate / N,N-dimethyl-formamide / 120 °C 3: N-Bromosuccinimide / chloroform / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium tert-butylate / tert-Amyl alcohol / 4 h / 110 °C 2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 110 °C 3: N-Bromosuccinimide / chloroform / 48 h / Darkness View Scheme | |
Multi-step reaction with 3 steps 1.1: potassium tert-butylate / tert-Amyl alcohol / 5 h / 110 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 130 °C / Inert atmosphere 2.2: 130 °C / Inert atmosphere 3.1: N-Bromosuccinimide / chloroform / 2 h / 50 °C / Inert atmosphere View Scheme |
2-hexyldecan-1-ol
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 120 °C 3: N-Bromosuccinimide / chloroform / 20 °C View Scheme |
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 110 °C 2: N-Bromosuccinimide / chloroform / 48 h / Darkness View Scheme |
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
Conditions | Yield |
---|---|
Stage #1: 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione; 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole With tris-(dibenzylideneacetone)dipalladium(0); Aliquat (at)366; triphenylphosphine In water; toluene for 0.25h; Schlenk technique; Inert atmosphere; Stage #2: With potassium phosphate In water; toluene at 115℃; for 16h; Schlenk technique; Inert atmosphere; Sealed tube; | 97% |
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
Conditions | Yield |
---|---|
Stage #1: 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione; 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole With tris-(dibenzylideneacetone)dipalladium(0); Aliquat (at)366; triphenylphosphine In water; toluene Schlenk technique; Inert atmosphere; Stage #2: With potassium phosphate In water; toluene at 115℃; Schlenk technique; Inert atmosphere; Sealed tube; | A 87% B 6.6% |
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
2-Ethynylanthracene
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In toluene at 60℃; for 8h; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique; | 75% |
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
C15H15BF2N2
Conditions | Yield |
---|---|
Stage #1: 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In tetrahydrofuran Schlenk technique; Inert atmosphere; Stage #2: C15H15BF2N2 In tetrahydrofuran at 60℃; for 3h; Inert atmosphere; | 75% |
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
phenylacetylene
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In toluene at 60℃; for 8h; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique; | 72% |
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
tributyl(thien-2-yl)stannane
3,6-di([2,2'-bithiophen]-5-yl)-2,5-bis(2-hexyldecyl)pyrrolo [3,4-c]pyrrole-1,4(2H,5H)-dione
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine In toluene at 90℃; for 24h; Stille Cross Coupling; Inert atmosphere; | 72% |
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
2-ethynylnaphthalene
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In toluene at 60℃; for 8h; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique; | 67% |
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
C78H124N2O2S4
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In toluene Heating / reflux; |
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
2-(4-dodecylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 115℃; for 24h; Suzuki coupling; | 1.062 g |
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
3,6-bis(5'-bromo-[2,2'-bithiophen]-5-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine / toluene / 24 h / 90 °C / Inert atmosphere 2: N-Bromosuccinimide / chloroform / 6 h / 20 °C / Inert atmosphere; Darkness View Scheme |
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
Conditions | Yield |
---|---|
With palladium diacetate; N-ethyl-N,N-diisopropylamine In toluene Inert atmosphere; Reflux; |
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
2-([2,2'-bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
Stage #1: 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione; 2-([2,2'-bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran for 0.5h; Suzuki Coupling; Inert atmosphere; Reflux; Stage #2: With potassium phosphate In tetrahydrofuran; water Suzuki Coupling; Inert atmosphere; Reflux; |
3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione
4,4,5,5-tetramethyl-2-(12,22:25,32-terthiophen-15-yl)-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
Stage #1: 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione; 4,4,5,5-tetramethyl-2-(12,22:25,32-terthiophen-15-yl)-1,3,2-dioxaborolane With tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran for 0.5h; Suzuki Coupling; Inert atmosphere; Reflux; Stage #2: With potassium phosphate In tetrahydrofuran; water Suzuki Coupling; Inert atmosphere; Reflux; |
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