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2 protocols using 4 iodoaniline

1

Synthesis and Characterization of Carbazole Derivatives

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Reagent
grade carbazole, p-bromonitrobenzene, copper iodide,
1,10-phenantroline, potassium
carbonate, hydrazine monohydrate, pyridine, acetic anhydride, cesium
carbonate, palladium on charcoal, tetrabutyl ammonium hexafluorophosphate
(TBAPF6), FeCl3, 4-iodoaniline, 4-iodobenzoic
acid, Cu2O, and 1,4,5,8-naphthalenetetracarboxylic dianhydride
were purchased from Sigma-Aldrich and were used as-received. Reagent
grade 1,2-cyclohexane anhydride and 1,2,4,5-cyclohexane dianhyride
were purchased from TCI Co., Ltd. and used as-received. Amino-phenyl
carbazole (APC) was stored as its HCl salt (Supporting Information, SI), and liberated before
use. Compound D1 is the precursor to the APC·HCl salt. Compound D2 was synthesized through
esterification of p-iodobenzoic acid followed by
cuprous oxide mediated carbazole coupling (SI). Details of the synthesis and characterization of APCCDI and APCNDI are provided as SI (Figures S1–S18).
UV/vis
absorption spectroscopy, electrochemistry, in situ UV/vis absorption,
and resonance Raman spectroelectrochemical experiments were conducted
in spectroscopic (UVASOL) grade dichloromethane (Merck).
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2

Chemical Synthesis of Nitro, Azo, and Halogenated Compounds

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Materials Nitrobenzene (99%), nitrosobenzene (97%), azoxybenzene, azobenzene (98%), hydrazobenzene, phenylhydroxylamine (97%), 4-chloroNitrobenzene (99%), 4chloroaniline (98%), 4-chlorobenzaldehyde (97%), 4-chlorobenzylalcohol (99%), 4-iodoNitrobenzene (98%), 4-iodoaniline (98%), 4-iodotoluene (99%), methanol (99.9%) and 1-butanol (99.7%) were all obtained from Sigma Aldrich. Potassium permanganate ($99%) was obtained from Fluka as was maleic acid ($98%). Metal precursors used were platinum nitrate (assay 15.14%) supplied by Johnson Matthey and palladium(II)nitrate hydrate procured from Sigma Aldrich. Research grade hydrogen was supplied by BOC. All chemicals were used as supplied.
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