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3 protocols using perylene 3 4 9 10 tetracarboxylic dianhydride

1

Synthetic Procedures for Organic Semiconductors

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The solvents dimethylsulfoxide (DMSO), dimethyl acetamide, chloroform (CHCl3), methanol (CH3OH), acetone, 1,4-dioxane, tetrahydrofuran (THF) and toluene were dried and distilled by well known standard procedures39 and kept in a glovebox for further use. Fluorene (1), 4,7-dibromobenzo[c]-1,2,5-thiadiazole (7), 9-(heptadecan-9-yl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (M3) and perylene-3,4,9,10-tetracarboxylic dianhydride were purchased from Sigma-Aldrich (USA) and was used directly without purification. 2-Bromo-9,9-dioctylfluorene (2), 2-bromo-7-nitro-9,9-dioctylfluorene (3), 2-amino-7-bromo-9,9-dioctylfluorene (4), 2,7-dibromo-9,9-dioctyl-9H-fluorene (5) and 4,4,5,5-tetramethyl-2-(4-octylthiophene-2-yl)-1,3,2-dioxaborolane (6) were synthesized by reported literature procedures.40–42 (link) 2,2′-(9,9-Dioctyl-9H-fluoren-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (M2) and 4,7-bis(4-octylthiophen-2-yl)benzo[c]-1,2,5-thiadiazole (M4) were synthesized by reported methods with modified reaction conditions and improved yields43,44 (link) (details were given in ESI).
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2

Synthesis of Doped Perylene Dianhydride Nanocomposites

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Aniline, chloroplatinic
acid hexahydrate (H2PtCl6, 6H2O,
≥37.50% Pt basis), perylene-3,4,9,10-tetracarboxylic dianhydride,
ammonium persulfate [(NH4)2S2O8] (APS), and titanium(IV) isopropoxide [Ti{OCH(CH3)2}4] were bought from Sigma-Aldrich and were
used as supplied, except Aniline which was distilled before use. Methanol
(HPLC Grade) was supplied by S D Fine-Chem Limited. Deionized water
(18 MU cm, Millipore Milli-Q water) was used to prepare solutions
where necessary.
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3

Synthesis of Siloxane-based Functional Materials

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Octamethylcyclotetrasiloxane (D4, 98%, Sigma-Aldrich), trifluoromethanesulfonic acid (triflic acid, 99%, Sigma-Aldrich), heptamethylcyclotetrasiloxane (tech-95, Gelest), trivinylmethylsilane (95%, Gelest), platinum(0)-1,3-divinyl-1,1,3,3-tertramethyldisiloxane in xylene (Pt catalyst, 2% of Pt, Sigma-Aldrich), perylene-3,4,9,10-tetracarboxylic dianhydride (97%, Sigma-Aldrich), and solvents were used as purchased. CB pearls 2000 (BP-2000) were offered by Cabot Corporation, silica nanoparticles (20 nm) were purchased from Sigma-Aldrich, and PTFE nanoparticles (MPD170, 20-50 nm) were purchased from DuPont. All the chemicals were used directly without further treatment.
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