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, hexylphenyl)-N,N-diphenyl-4H-indeno[1,2-b]thiophen-6-amine : Under argon, Pd2dba3 (4 mg, 4.37 ?mol) and tri-tertbutylphosphine tetrafluoroborate (2.54 mg, 8.75 ?mol) were dissolved with anhydrous toluene (5 mL), HRMS (ESI): [M+H] +. = Synthesis of 4,4-bis, vol.437

, Before refluxed for 48h, we added potassium tert-butoxide (161.94 mg, 1.44 mmol, 3.3 eq) and the resulting mixture was stirred for 30min at room temperature. The melt was filtered through celite and poured into HCl (2M). The organic phase was extracted with DCM, ?mol) and diphenylamine (81.4 mg, 481.0 ?mol) in anhydrous toluene (10 mL) was added

H. Nmr, CDCl3, 400 MHz): ? = 7.28 (d, 1H, J=8.2Hz, Har), 7.22 (d, 1H, J=8.2Hz, Har), 7.22 (s, 1H, Har), 7.18 (m, 4H, Har), 7.04 (m, 7H, Har), 6.98 (m, 7H, Har), 6.95(m, 1H, Har), 6.93 (d, 1H, J=2.1Hz, Har), 2.53 (t, 4H, CH2) 1.55 (m, 4H, CH2), 1.28 (m, 12H, CH2), 0.87

, HRMS

H. Nmr, CDCl3, 200 MHz): ? =7.54 (d, 1H, J1=4Hz), 7.42 (m, 2H), 7.31 (d, 1H, J1=4Hz), 7.22 (d, 1H, J1=4Hz), 7.16 (d, 1H, J1=4Hz), 7.07 (m, 4H), 6.92 (m, 2H), 6.87 (m, 4H), 3.97 (t, 4H, J1=6.5Hz), 1.81 (m, 4H), 1.49 (m, 4H), 1.39-1.35 (m, 8H), 0.94 (m, 6H). 13 C NMR (CDCl3, 50 MHz): ?

, '-diyl)bis(N,N-bis(4-(hexyloxy)phenyl) aniline) as a indesirable product : water. The organic phase was dried with sodium sulphate and evaporated. The crude product was purified by chromatography with 70:30 dichloromethane:hexane eluent to give, vol.5

H. Nmr, CDCl3, 200 MHz): ? = 9.86(s, 1H), 7.63 (dd, 1H, J1=3.7 Hz, J2=0.9Hz), 7.63(ABQ, 2H, J1=4.1Hz, ??AB= 39.76 Hz), 7.40 (dd, 1H, J1=5.1Hz, J2=0.9Hz), vol.7

C. Nmr-(cdcl3 and . Mhz,

, 16 (216 mg, 645.85 µmol, 1eq) was dissolved in chloroform (20 ml) at-10°C. A solution of N-bromosuccinimide (115 mg, 645.85 µmol, 1eq) in acetic acid/chloroform mixture (1:1 8 ml) was added dropwise. After 40 minutes the solution was quenched with water and extracted with chloroform. The organic phase was washed with water, vol.3

H. Nmr, C2D4Cl4, 200 MHz): ? = 9.89 (s, 1H), 7.69 (ABQ, 2H, J1=4.1Hz, ??AB= 32.15Hz), vol.7

, Anal. calcd for, vol.13, issue.5, pp.37-77

. Pd2dba3, 54 mg, 6.05 µmol, 0.05 eq) and P(2-furyl)3 (11, p.23

, The organic phase was extracted with chloroform, washed with water, dried over Na2SO4 and concentrated. The crude solid was chromatographed on silica using dichloromethane/nhexane : 5/5 as eluent to afford corresponding aldehyde greenish solid

H. Nmr, C2D4Cl4, 200 MHz, 50°C): ? = 9.87(s, 1H), 7.76 (d, 1H, J1=4.1Hz), 7.63 (m, 2H), 7.32 (m, 2H), 7.24 (d, 1H, J1=4.1Hz), 7.1 (m, 1H). 13 C NMR (C2D4Cl4, 50 MHz, 50°C): ? = 182, vol.23, p.53

, mmol) was dissolved in distilled THF (15 mL) then nBuLi (2.5M, 734 µL, 1.83 mmol, 1.2 eq) was added at-78 °C. The solution was stirred for an hour

, °C before adding tributyltin chloride (621 µL, vol.2, p.29

, eq) at-78 °C. The solution was allowed to reach room temperature and stirred for dried over Na2SO4 and concentrated. The crude solid was chromatographed on silica using dichloromethane/n-hexane : 4/6 as eluent to

H. Nmr, CDCl3, 400 MHz): ? =8.07 (s, 1H), 7,32 (s, 1H), 7.31 (d, 1H, J1= 8.3 Hz), 7.24-7.19 (m, 4H), 7.15 (d, 1H, J1=2Hz),7.06 (m, 2H)

, (diphenylamino)-4,4-bis(4-hexylphenyl)-4H-indeno[1,2-b]thiophen-2yl)-3,4-dinitrothiophen-2-yl)benzoate : Under argon, Synthesis, vol.4, issue.5

, mg, 240.36 µmol, 1 eq), ethyl 4-bromobenzoate (71.58 mg, 312.47 µmol, vol.1

, Ditert-butyl(methyl)phosphonium tetrafluoroborate (9.54 mg, 38.46 µmol, 0.16 eq), palladium acetate (4.32 mg, 19.23 µmol, 0.08 eq) and cesium carbonate (156.63 mg, 480.72 µmol, 2 eq) was dissolved in anhydrous toluene (20 mL) and refluxed overnight. The mixture was then poured into HCl (2M). The organic phase was extracted with chloroform

H. Nmr, CDCl3, 400 MHz): ? =8.36 (td, 2H, J1=8.5Hz, J2=1.8Hz), 7.76 (td, 2H, J1=8.5Hz, J2=1.8Hz), 7.74 (s, 1H), 7.57 (d, 1H, J1=8.3Hz), 7.48 (s, 2H), 7.46-7.43 (m, 4H), 7.39 (d, 1H, J1=2Hz), 7.29 (m, 2H), 7.287.22 (m, 10H), 7.18 (dd, 1H, J1=8.3Hz, J2=2Hz), 4.64 (q, 2H, J1=7.1Hz), 2.77 (t, 4H, J1=7.9Hz), 1.80 (m, 4H), 1.64 (t, 3H, J1=7.1Hz), 1.52 (m, 10H), 1.09 (m, 6H). 13 C NMR

, 2'-dione: ? Lawesson method : Lawesson's reagent (0.533 g, 1.32 mmol) was dissolved in dry Toluene (10 ml) and heated at 100°C. Then, a solution of 4-(2-hexyldecyl)-4H-thieno[3,2-b]pyrrole-5,6dione (0.700 g, 2.64 mmol) in dry toluene (20 ml) was added. The reaction was heated to 100°C and stirred 4 hours. After cooling, water was added and the product was extracted with diethyl ether, washed with brine and dried over Na2SO4. After removal of the solvent the crude product was subjected to silica column chromatography

?. Method,

, ethylhexyl)-4,6-dihydro-5H-thieno[3,2-b]pyrrol-5-one (384 mg, 1.53 mmol, 1.0 equiv.), 4-(2-ethylhexyl)-4H-thieno, A dry flask was charged with 4, vol.1, p.53

, The reaction mixture was allowed to stir at 110°C overnight. Upon cooling, the mixture was poured into water, extracted three times with chloroform, glacial acetic acid (20 mL)

H. Nmr, CDCl3, 400 MHz): ? = 7.52 (d, 2H, J1=5.2Hz), 6.79 (d, 2H, J1=5.2Hz), 3.69 (m, 4H), 1.85 (m, 2H), 1.42-1.28 (m, 16H), 0.93-0.86 (m, 12H). 13 C NMR (CDCl3, 100 MHz): ? =171

2. Hcl, dried over sodium sulphate and concentrated by rotary evaporation. The crude product was purified via silica gel chromatography (1:1 dichloromethane/hexane) to provide (Z)-4-(3-(2-bromo-4-(2-ethylhexyl)-5-oxo-4,5-dihydro-6H-thieno[3,2-b]pyrrol-6-ylidene)-1-(2ethylhexyl)-2-oxoindolin-6-yl

H. Nmr, CDCl3, 400 MHz): ? = 10.08 (s, 1H), vol.9, p.73

. Hz, 7.35 (dd, 1H, J1=8.2Hz, J2=1.8Hz), 7.06 (d, 1H, J1=1.8Hz), 6.79 (s, 1H), 3.77 (m, 2H), 3.62 (m, 2H), 1.91 (m, 2H), 1.80 (m, 2H), 1.46-1.25 (m, 16H), 0.89-0.95 (m, 12H). 13 C NMR (CDCl3, 100 MHz): ? = 191, vol.68

, Anal. calcd for, vol.37, issue.43, pp.65-77

, (diphenylamino)phenyl)-4-octylthiophen-2-yl)-1,1'-bis(2-ethylhexyl)2,2'-dioxo-[3,3'-biindolinylidene]-6-yl)benzaldehyde: Under argon, 4-(3-octylthiophen-2-yl)-N,Ndiphenylaniline (200 mg, 909.8 µmol) was dissolved in distilled THF (10 mL) then n-BuLi ( 2.5M, 218 µL, 545 µmol) was added at-78°C. The solution was stirred for an hour at-60°C before adding Bu3SnCl (185 µL, 682.3 µmol) at-78°C. diethyl ether, dried with Na2SO4, filtered and concentrated under reduced pressure. The resulting oil was engaged without any further purification in a Stille coupling reaction with (E)-4-(6'-bromo-1,1'-bis(2-ethylhexyl)-2,2'-dioxo-[3,3'-biindolinylidene]-6yl)benzaldehyde (200 mg, 298.6 µmol), Pd2dba3 (10.9 mg, 11.9 µmol) and P(o-tolyl)3 (7.27 mg, 23.9 µmol) dissolved in anhydrous toluene (15 mL) and refluxed for 24 hours, The organic phase was extracted with CHCl3, washed with HCl

, dried over Na2SO4 and concentrated under reduced pressure. The crude solid was purified by chromatography on silica gel using diethyl ether/n-hexane 3:7 as eluent to afford the desired product as a greenish solid

H. Nmr, CDCl3, 400 MHz): ? = 10.08 (s, 1H), 9.22 (ABQ, 2H, J1=8.3Hz, ??AB= 25.02 Hz), 7.89 (ABQ, 4H, J1=8.3Hz, ??AB= 77.14 Hz), 7.35-7.27 (m, 9H), 7.16 (m, 4H), 7.10 (m, 2H), 7.08-7.04 (m, 2H), 7.00 (dd, 2H, J1=9Hz, J2=1.6Hz), 3.75 (m, 4H), 2.70 (m, 2H), 1.91 (m, 2H), 1.71-1.60 (m, 5H), 1.48-1.26 (m, 23H), 0.99-0.86 (m, 15H). 13 C NMR (CDCl3, 100 MHz): ? = 191, vol.68

, diphenylamino)phenyl)-4-octylthiophen-2-yl)-1,1'-bis(2ethylhexyl)-2,2'-dioxo-[3,3'-biindolinylidene]-6-yl)phenyl)acrylic acid: Under argon, (E)-4-(6'-(5-(4-(diphenylamino)phenyl)4-octylthiophen-2-yl)-1,1'-bis(2-ethylhexyl)-2,2'the solid dissolved in chloroform, The organic phase was washed with HCl solution (2 M), dried on Na2SO4 and concentrated. The crude solid was purified by chromatography on silica gel using DCM, DCM/MeOH 98:2 and DCM/MeOH/Acetic acid 90:5:5 as eluent to afford (E)

H. Nmr, THF d8, 400 MHz): ? = 9.39 (dd, 2H, J1=8.5Hz, J2= 22.4 Hz), 8.29 (s, 1H), 8.03 (ABQ, 4H, J1=8.3Hz, ??AB= 101.95 Hz), 7.45 (s,1H), p.100

. Mhz,

, HRMS

, 2-b]pyrrol-6-ylidene)-1-(2-ethylhexyl)-2-oxoindolin-6yl)benzaldehyde : Under argon, 4-(3-octylthiophen-2-yl)-N,Ndiphenylaniline (200 mg, 909.8 µmol) was dissolved in distilled THF (10 mL) then n-BuLi ( 2.5M, 218 µL, 545 µmol) was added at-78°C. The solution was stirred for an hour at-60°C before adding Bu3SnCl (185 µL, 682.3 µmol) at and the organic phase was extracted with diethyl ether, dried with Na2SO4, filtered and concentrated under reduced pressure. The resulting oil was engaged without any further purification in a Stille coupling reaction with (Z)-4-(3-(2-bromo-4-(2ethylhexyl)-5-oxo-4,5-dihydro-6H-thieno[3,2-b]pyrrol-6-ylidene)-1-(2-ethylhexyl)-2oxoindolin-6-yl)benzaldehyde (200 mg, 296 µmol), Pd2dba3 (10.9 mg, 11.9 µmol) and P(otolyl)3 (7.27 mg, 23.9 µmol) dissolved in anhydrous toluene (15 mL) and refluxed for 24 hours, The organic phase was extracted with CHCl3, washed with HCl, vol.3

H. Nmr, CDCl3, 400 MHz): ? = 10.08 (s, 1H), vol.9, p.29

. Hz, (diphenylamino)phenyl)-4-octylthiophen-2-yl)-4-(2ethylhexyl)-5-oxo-4,5-dihydro-6H-thieno[3,2-b]pyrrol-6-ylidene)-1-(2-ethylhexyl)-2-oxoindolin6-yl)phenyl)acrylic acid: Under argon, 7.39-7.26 (m, 8H), 7.17-7.03 (m, 9H), 6.78 (s, 1H), 3.81 (m, 2H), 3.68 (m, 2H), 2.66 (t, 2H, J1=7.3Hz), 1.97 (m, 1H), 1.88 (m, 1H), 1.72-1.63 (m, 5H), 1.53-1.26 (m, 23H), 0.99-0.89 (m, 15H). 13 C NMR (CDCl3, 100 MHz): ? = 191, vol.73

H. Nmr-(thf-d, 400 MHz): ? = 9, p.31

. Hz, 7.44 (m, 2H), 7.36 (m, 2H), 7.30-7.26 (m, 5H), 7.13-7.02 (m, 8H), 7.00 (s, 1H), 3.84 (m, 2H), 3.72 (m, 2H), 2.71 (t, 2H, J1=7.3Hz), 2.02 (m, 1H), 1.93 (m, 1H), 1.50-1.26 (m, 28H), 0.99-0.87 (m, 15H). 13 C NMR

, HRMS

, ethylhexyl)-5,5'-dioxo-4,4',5,5'-tetrahydro-[6,6'-bithieno[3,2-b]pyrrolylidene]-2yl)phenyl)acrylic acid: Under argon, (E)-4-(2'-(5-(4(diphenylamino)phenyl)-4-octylthiophen-2yl)-4'-(2-ethylbutyl)-4-(2-ethylhexyl)-5,5'dioxo-4,4',5,5'-tetrahydro-[6,6'-with HCl solution (2 M), dried on Na2SO4 and concentrated, The crude solid was purified by chromatography on silica gel using DCM, DCM/MeOH 98:2 and DCM/MeOH/Acetic acid 90:5:5 as eluent to afford (E)

H. Nmr-(thf-d, 400 MHz): ? = 8.20 (s, 1H), 8.07 (m, 2H), 7.96-7.86 (m, 2H), 7.40-7.25 (m, 8H), 7.137.03 (m, 8H), 3.75 (m, 4H), 2.70 (t, 2H, J1=7.3Hz), 1.92 (m, 2H), 1.69 (m, 5H), 1.41-1.26 (m, 23H), 0.990.89 (m, 15H). 13 C NMR (THF-d, 100 MHz): ? = 153, vol.98

H. Esi,

, hexylphenyl)-4H-indeno[1,2-b]thiophen-2-yl)1,1'-bis(2-ethylhexyl)-2,2'-dioxo, p.467

, 537 µmol, 1.15 eq) was added at-78 °C. The solution was stirred for an hour at-60 °C before adding trimethyltin chloride solution (1M, 700 µL, 700 µmol, 1.5 eq) at-78 °C. The solution was allowed to reach room temperature and stirred for 2 hours. The reaction was quenched with a saturated solution of ammonium chloride and the organic phase was extracted with pentane, washed with water and dried on Na2SO4, filtered and concentrated under vacuum. The resulting oil was engaged without any further purification in a, µmol) was dissolved in distilled THF (20 mL) then n-BuLi (1.5M, 383 µL

, 66 µmol, 0.04 eq) in anhydrous toluene (20 ml) and refluxed overnight. The mixture was then poured into HCl (2M). The organic phase was extracted with chloroform, washed with water, dried over Na2SO4 and concentrated. The crude solid was chromatographed on silica using, eq) and P(o-tolyl)3 (5.68 mg, vol.18

H. Nmr, CDCl3, 400 MHz): ? = 10.08 (s, 1H), 9.21 (ABQ, 2H, J1=8.3Hz, ??AB= 26.83 Hz), 7.89 (ABQ, 4H, J1=8.3Hz, ??AB= 76.74 Hz), 7.33-7.27 (m, 4H), 7.23-7.18 (m, 5H), 7.11-6.95 (m, 17H)

, Anal. calcd for, vol.86, issue.93

, Synthesis of 2-cyano-3-(4-((E)-6'-(6-(diphenylamino)-4,4-bis(4-hexylphenyl)-4H-indeno[1,2b]thiophen-2-yl)-1,1'-bis(2-ethylhexyl)-2,2'-dioxo-[3,3'-biindolinylidene]-6-yl)phenyl)acrylic acid: Under argon, vol.4

, yl)benzaldehyde (230 mg, 184 µmol, p.1

, cyanoacetic acid (157 mg, vol.1, p.84

, HCl solution (2M), dried on Na2SO4 and concentrated. The crude solid was chromatographied on silica using DCM first then DCM/MeOH : 90/5 and then DCM/MeOH

H. Nmr, THF d8, 400 MHz): 8.03 (dd, 2H, J1=8.4Hz, J2=11.3Hz), 8.30 (s, 1H), 8.03 (ABQ, 4H, J1=8.4Hz, ??AB= 50.8 Hz), 7.59 (s,1H), 7.40-7.30 (m, 3H), 7.20-6.95 (m, 21H), 3.80 (m, 4H), 2.55 (m, 4H), 1.621.29 (m, 34H), 0.98-0.86 (m, 18H). 13 C NMR (THF d8, 100 MHz): ? = 169, vol.49

, HRMS

, hexylphenyl)-4H-indeno[1,2-b]thiophen-2-yl)4-(2-ethylhexyl)-5-oxo-4,5-dihydro-6H-thieno[3,2-b]pyrrol-6-ylidene)-1-(2-ethylhexyl)-2oxoindolin-6-yl)benzaldehyde: Under argon, 4,4-dioctyl, p.303

, 364 µmol, 1.2eq) was added at-78 °C. The solution was stirred for an hour at-60 °C before adding tributyltin chloride (123 µL, 455 µmol, 1.5 eq) at-78 °C. pentane, washed with water and dried on Na2SO4, filtered and concentrated under vacuum. The resulting oil was engaged without any further purification in a, µmol) was dissolved in distilled THF (10 mL) then n-BuLi (2.5M, 151 µL, vol.222

. Pd, 5% mol). The products were dissolved in anhydrous toluene (20mL) and refluxed overnight. The mixture was then poured into HCl (2M). The organic phase was extracted with chloroform, washed with water, dried over Na2SO4 and concentrated. The crude solid was, vol.11

H. Nmr-(cdcl3, 400 MHz): ? = 10.08 (s, 1H), vol.9, p.73

. Hz, 7.39 (s, 1H), 7.37 (dd, 1H, J1=8.2Hz, J2=1.8Hz), 7.28 (d, 1H, J1=8.2Hz), 7.24 (s, 1H), 7.21 (m, 2H), 7.20 (m, 2H), 7.09-7.01 (m, 15H), 6.95 (dd, 1H, J1=8.2Hz, J2=1.8Hz), 6.76 (s, 1H), 3.79 (m, 2H), 3.67 (d, 2H, J1=7.7Hz), 2.56 (t, 4H, J1=7.7Hz), 1.94 (m, 1H), 1.87 (m, 1H), 1.59(m, 4H), 1.48-1.26 (m, 28H), 0.89-0.95 (m, 18H). 13 C NMR (CDCl3, 100 MHz): ? = 191, vol.76

, Synthesis of (E)-2-cyano-3-(4-((Z)-3-(2-(6-(diphenylamino)-4,4-bis(4-hexylphenyl)-4Hindeno[1,2-b]thiophen-2-yl)-4-(2-ethylhexyl)-5-oxo-4,5-dihydro-6H-thieno[3,2-b]pyrrol-6ylidene)-1-(2-ethylhexyl)-2-oxoindolin-6-yl)phenyl)acrylic acid: Under argon

, ethylhexyl)-2oxoindolin-6-yl)benzaldehyde (138 mg, 109.98 µmol), cyanoacetic acid, vol.46, p.77

, A catalytic amount of piperidine was added and the solution was refluxed for 3 hours. Solvent was removed under reduced pressure and the solid redissolved in chloroform. The organic phase was washed with HCl solution (2M), dried on Na2SO4 and concentrated. The crude solid was chromatographed on silica using DCM, mg, 1mmol, 5eq), were dissolved in a mixture of acetonitrile (6mL) and chloroform (4mL), vol.98

H. Nmr, THF-d8, 400 MHz): ? = 9.31 (d, 1H, J1=8.3Hz), 8.29 (s, 1H), 8.14 (m, 2H), 7.89 (m, 2H), 7.53 (s, 1H), 7.43 (d, 1H, J1=8.3Hz), 7.35 (d, 1H, J1=8.3Hz), 7.27 (s, 1H), 7.22-7.18 (m, 4H), 7.16 (m, 1H), 7.137.10 (m, 4H), 7.06-7.04 (m, 9H), 6.99-6.93 (m, 3H), 3.83 (m, 2H), 3.72 (d, 2H, J1=7.7Hz), 2.56 (t, 4H, J1=7.7Hz), 2.01 (m, 1H), 1.94 (m, 1H), 1.59(m, 4H), 1.48-1.29 (m, 28H), 0.98-0.86 (m, 18H). 13 C NMR (THF-d8, 100 MHz): ? = 168

, HRMS

, 4H-indeno[1,2-b]thiophen-2-yl)4,4'-bis(2-ethylhexyl)-5,5'-dioxo-4,4',5,5'-tetrahydro, vol.263, p.12

, 19 µmol) at-78°C. The solution was allowed to reach room temperature and stirred for 2 hours. The reaction was quenched with a saturated solution of ammonium chloride and the organic phase was extracted with diethyl ether, dried with Na2SO4, filtered and concentrated under reduced pressure. The resulting oil was engaged without any further purification in a, µmol) was added at-78°C. The solution was stirred for an hour at-60°C before adding Bu3SnCl (74 µL, vol.343

, Pd2dba3 (4.2 mg, 4.58 µmol) and P(o-tolyl)3 (2.8 mg, 9.15 µmol) dissolved in anhydrous toluene (15 mL) and refluxed for 24 hours. The mixture was then poured into HCl (2 M). The organic phase was extracted with CHCl3, yl)benzaldehyde (125 mg, 183.04 µmol)

, dried over Na2SO4 and concentrated under reduced pressure. The crude solid was purified by chromatography on silica gel using DCM/n-hexane 2:8 as eluent to afford the desired product as a greenish solid

H. Nmr, (m, 14H), 6.98 (dd, 1H, J1=8.2Hz, J2=2Hz), 6.85 (s, 1H), 3.71-3.66 (m, 4H), 2.58 (t, 4H, CD2Cl2, 400 MHz): ? = 9.99 (s, 1H), 7.86 (m, 4H), 7.36 (s, 1H), 7.33 (d, 1H, J1=8.2Hz), 7.25 (m, 1H), 7.16 (d, 1H, J1=2Hz), 7.13 (s, 1H)

. Anal,

, Synthesis of (E)-2-cyano-3-(4-((E)-2'-(6-(diphenylamino)-4,4-bis(4-hexylphenyl)-4H-indeno[1,2b]thiophen-2-yl)-4,4'-bis(2-ethylhexyl)-5,5

, 2-yl)benzaldehyde (150 mg, 119 µmol), cyanoacetic acid (101 mg, 1.19 mmol), were dissolved in a mixture of acetonitrile (6mL) and chloroform (4mL)

, Solvent was removed under reduced pressure and the solid redissolved in chloroform. The organic phase was washed with HCl solution (2M), dried on Na2SO4 and concentrated, The crude solid was chromatographed on silica using DCM, DCM/MeOH 98:2 and then DCM/MeOH/Acetic acid 90:5:5 as

H. Nmr, THF-d8, 400 MHz):? = 8.17 (s, 1H), 7.94 (m, 2H), 7.69 (m, 2H), 7.43 (s, 1H), 7.28 (m, 1H), 7.20 (m, 5H), 7.14 (m, 5H), 7.06 (m, 8H), 6.99-6.92 (m, 4H), 3.71 (m, 4H), 2.58 (t, 4H, J=7.6Hz), 1.94 (m, 2H), 1.60 (m, 4H), 1.40-1.31 (m, 22H), 0.97-0.87 (m, 18H). 13 C NMR (THF-d8, 100 MHz): ? = 168, vol.65

H. Esi,

, Synthesis from Chapter

, 2-dioxaborolan2-yl)phenyl)aniline: A mixture of 4-bromo-N,N-bis(4-(hexyloxy)phenyl)aniline (2.00 g, 3.50 mmol, vol.4, pp.5-6

, 93 g,3.67 mmol)

. Pd, 105 mmol) in anhydrous dimethyl sulfoxide (25 crude product was extracted into ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. After removing solvent under reduced pressure, the residue was purified by column chromatography (ethyl acetate/petroleum ether 2%) on silica gel to

H. Nmr, CDCl3, 400 MHz): ? = 7.44 (d, J=8.4 Hz, 2H), vol.1, pp.25-37

, 0.88 (t, J=6.8 Hz, 6H). 13 C NMR (CDCl3, 100 MHz): ?= 155, vol.67

, 3-octylthiophen-2-yl)phenyl)aniline : Under argon

, 2-bromo-3-octylthiophene (746 mg, 2.78 mmol

. Pd, 11 mmol) were dissolved in degassed toluene, aqueous solution of K2CO3 (4.16 mL, 8.32 mmol) was added and the mixture was heated at 100°C overnight before being poured into water. The organic phase was extracted with Et2O, dried on Na2SO4 and concentrated. The crude oil was chromatographed on silica using n-hexane/DCM 8:2 as eluent to afford pale yellow oil 6

H. Nmr, CDCl3, 400 MHz): ? = 7.10 (ABq, 4H, ??ab=114.0Hz, J=8.5Hz), 7.07 (ABq, 2H, ??ab=80.3Hz, J=5.0Hz), 6.99 (ABq, 8H, ??ab=98.4Hz, J=8.8Hz), 3.97 (t, 4H, J=6.5Hz), 2.67 (t, 2H, J=7.8Hz), 1.90-1.70 (m, 4H), 1.64-1.20 (m, 24H), 0.99-0.83 (m, 9H). 13 C NMR (CDCl3, 100 MHz

, (3and the organic phase was extracted with diethyl ether, dried with Na2SO4, filtered and concentrated under reduced pressure. The resulting oil was engaged without any further purification in a Stille coupling reaction with (E)-4-(6'-bromo-1,1'-bis(2ethylhexyl)-2,2'-dioxo-[3,3'-biindolinylidene]-6-yl)benzaldehyde (200 mg, 298.6 µmol), Pd2dba3 (10.9 mg, 11.9 µmol) and P(o-tolyl)3 (7.27 mg, 23.9 µmol) dissolved in anhydrous toluene (15 mL) and refluxed for 24 hours, The organic phase was extracted with CHCl3, washed with HCl

H. Nmr, 17 (d, 1H, J1=8.4Hz), 7.99 (m, 2H), 7.79 (m, 2H), 7.32 (dd, 1H, J1=8.4Hz, J2=1.7Hz),7.29 (s, 1H), 7.28 (dd, 1H, J1=8.4Hz, J2=1.7Hz), 7.27 (m, 1H), 7.25 (m, 1H), 7.10 (m, 4H), vol.9, p.24

C. Nmr-(cdcl3,

. Anal,

, (hexyloxy)phenyl)amino)phenyl)4-octylthiophen-2-yl)-1,1'-bis(2ethylhexyl)-2,2'-dioxo-[3,3'chloroform. The organic phase was washed with HCl solution (2 M), dried on Na2SO4 and concentrated, The crude solid was purified by chromatography on silica gel using DCM, DCM/MeOH 98:2 and DCM/MeOH/Acetic, vol.87

H. Nmr, (m, 21H). 13 C NMR (THF d8, 100 MHz): ? = 168, THF d8, 400 MHz): ? = 9.32 (m, 2H), 8.35 (m, 1H), 8.05 (m, 2H), 7.73 (m, 2H), 7.34 (s, 1H), 7.24-7.17 (m, 4H), 7.09-7.06 (m, 5H), 6.91 (m, 2H), 6.87 (m, 5H), 3.97 (t, 4H, J1=6.4Hz), 1.98-1.92 (m, 2H), 1.79 (m, 4H), 1.67 (m, 2H), 1.55-1.33 (m, 44H), vol.17

, HRMS

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