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7 protocols using o dichlorobenzene

1

Synthesis of DCPD Novolac Epoxy Resin

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DCPD (from Sigma), aluminum(III)
chloride (AlCl3, from Alfa), TPC (from TCI), IPC (from
TCI), 2,6-dimethylphenol (from Acros), 2,3,6-dimethylphenol (from
Acros), and phenol DCPD novolac epoxy with an EEW of 250 g/equiv were
kindly supplied by Dainippon Ink and Chemicals Corporation under the
commercial name of HP-7200. 4-Dimethylaminopyrdine (DMAP, from Alfa),
Imi (from Acros), 2-MI (from Aldrich), TPP (from Alfa), and 2,4,5-TPI
(from Alfa) were used as received without purification. o-Dichlorobenzene (from Acros), N-methylpyrrolidone
(NMP from Tedia), DMAc (from Tedia), MEK (from Acros), and other solvents
used for the solubility test are HPLC or ACS grade and were used as
received without purification.
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2

Synthesis of Phloroglucinol Derivatives

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Chemicals were acquired from commercial sources and used as obtained. Phloroglucinol (99%), potassium carbonate (K2CO3), nitrobenzene, 4-aminophenylboronic acid pinacol ester, acetic acid (CH3COOH), and n-butanol were ordered from Sigma–Aldrich (St. Louis, MO, USA). Tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4), trifluoromethanesulfonic acid (≥98%), o-dichlorobenzene, and bromobenzonitrile (≥98%) were obtained from Acros (Maribor, Slovenia).
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3

Organic Solvent Preparation Protocol

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2-(2-Butoxyethoxy)ethanol (Acros Organics, Geel, Belgium, 99+%), 2,6-di-tert-butyl-4-methylphenol (BHT, Acros Organics, 99%), o-dichlorobenzene (Acros Organics, 99%), C6D4Cl2 (99 atom % D, Deutero GmbH, Kastellaun, Germany), acetone (analytical grade, POCH, Gliwice, Poland) and methanol (Stanlab, Lublin, Poland, analytical grade) were used as received.
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4

Synthesis of Organic Compounds

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Example 2

2-Bromotoluene was purchased from Oakwood Products. Urea, bromoethane, 2-bromopropane, tetrabutylammonium hexafluorophosphate, tris(4-bromophenyl)aminium hexachloroantimonate, anhydrous toluene, and anhydrous p-dioxane were purchased from Sigma Aldrich. Phenothiazine, sodium hydride (60% dispersion in mineral oil), bis(dibenzylideneacetone)palladium(0), sodium tert-butoxide, sulfur, iodine, o-dichlorobenzene (ODCB), anhydrous dichloromethane (DCM), anhydrous tetrahydrofuran, anhydrous N,N-dimethylformamide (DMF), and magnesium sulfate were obtained from Acros Organics. Tri-tert-butylphosphonium tetrafluoroborate was obtained from Oxchem. Silica gel and neutral alumina used for column chromatography were purchased from Silicycle and Sorbent Technologies, respectively. Ethyl acetate, hexanes, and diethyl ether were purchased from VWR. Solvents used for NMR spectroscopy were obtained from Cambridge Isotope Laboratories.

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5

Synthesis and Characterization of Fluorinated Benzamides

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Zinc powder was purchased from Sigma-Aldrich. Toluene, chloroform, dichloromethane, o-dichlorobenzene (DCB) and ethanol were purchased from Fisher. Silicon wafers having an oxide layer thickness of ~275 nm were purchased from Silicon Valley Microelectronics, Inc. (Santa Clara, CA). N-(3-Trimethoxysilylpropyl)-4-azido-2,3,5,6-tetrafluorobenzamide (PFPA-silane),45 N-(3-trimethoxysilylpropyl)-2,3,4,5,6-pentafluorobenzamide (PFB-silane),39 (link) and 11,11′-disulfanediylbis(undecane-11,1-diyl)bis(4-azido-2,3,5,6-tetrafluorobenzoate) (PFPA-disulfide)42 (Figure 1) were synthesized following previously reported procedures.
1H and 13C NMR data were recorded on a Bruker AMX-400 MHz spectrometer. Chemical shifts are reported as δ values (ppm) with CDCl3 (1H = 7.26, 13C = 77.16) as the internal standard. FTIR analysis was performed on a Nicolet iS10 spectrophotometer using a diamond attenuated total reflectance (ATR) attachment.
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6

Molecular Weight Characterization of P3HT

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Ten batches of P3HT (relative calibration, Table 2; universal calibration, Table S1) and F4TCNQ from TCI Chemicals were
used as received without further purification. The molecular weight
was measured with size exclusion chromatography (SEC) on an Agilent
PL-GPC 220 integrated high temperature GPC/SEC system in 1,2,4-trichlorobenzene
at 150 °C using relative calibration with polystyrene standards.
Solvents with purity >99% were purchased from Sigma-Aldrich (o-dichlorobenzene, chlorobenzene, p-xylene,
cyclohexanone, 1,2,4-trichlorobenzene) and Fisher Scientific (chloroform,
toluene).
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7

Characterization of P3HT and F4TCNQ Dopant

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P3HT was obtained from Ossila Ltd. (regioregularity ∼ 96%, number-average molecular weight of Mn ∼ 29 kg mol−1, polydispersity index ∼ 2.2). The regioregularity was determined with a 475 Agilent (Varian) MR 400 MHz spectrometer with CDCl3 as the solvent. The molecular weight was measured with size exclusion chromatography (SEC) on an Agilent PL-GPC 220 integrated high temperature GPC/SEC system in 1,2,4-trichlorobenzene at 150 °C using relative calibration with polystyrene standards. F4TCNQ was purchased from TCI Chemicals and used without further purification. Solvents with purity >99% were purchased from Sigma-Aldrich (o-dichlorobenzene, chlorobenzene, p-xylene, 1,2,4-trichlorobenzene) and Fisher Scientific (chloroform, toluene).
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