Selective and efficient synthesis of cyclic hexakis(thio-1,4-phenylene) through oxidative polymerization of diphenyl disulfide

Macromolecules

Volumn 30, Issue 15, 1997, Pages 4502-4503

  Miyatake, Kenji ^a   Yokoi, Yoshihiro ^a   Yamamoto, Kimihisa ^a   Tsuchida, Eishun ^a   Hay, Allan S ^b  

^a WASEDA UNIVERSITY   (Japan)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC POLYMERS; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOMERS; OXIDATION; POLYCONDENSATION; POLYMERIZATION; RING OPENING POLYMERIZATION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CYCLIC HEXAKISTHIOPHENYLENE; DIPHENYL DISULFIDE; MATRIX ASSISTED LASER DESORPTION IONIZATION; NUCLEOPHILIC SUBSTITUTION REACTION; OXIDATIVE POLYMERIZATION;

POLYPHENYLENE OXIDES;

EID: 0031192205     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma961740o     Document Type: Article

References (21)

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16. A 20 mL dichloromethane solution of diphenyl disulfid (4 mmol) was added dropwise to 60 mL of dichloromethane containing 23-dichloro-5,6-dicyano-p-benzoquinone (4 mmol), trifluoroacetic acid (0.08 mol), and trifluoroacetic anhydride (16 mmol) with a period of 2 days The mixture was stirred for another day to ensure the completion of the reaction and then poured into 500 mL of 37% hydrochloric acid diluted 1:9 with methanol to precipitate the oligomer. The crude product was treated with three portions of 100 mL of aqueous 5% NaOH solution to remove 2.3-dichloro-5,6-dicyano-p-hydroquinone. The resulting white powder was washed with water and methanol and dried at 20 °C under vacuum for 20 h.
17. The higher monomer concentration is possible by slowing the rate of addition over 2 days.
18. Linear gradient HPLC was performed on a Milton Roy CM4000 multiple solvent delivery system with a C8 Prime Sphere 4.6 × 250 mm column, THF and water as eluent solvents, and a UV detector at 300 nm. The total running time for each injection was 30 min. The gradient condition was as follows: at 0 min, THF 70%; at 20 min, THF 90%; at 25 min, THF 100%; at 27 min, THF 70%; at 30 min (end), THF 70%.
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21. Linear octakis(thio-1,4-phenylene) containing one disulfide at the end of the chain, which is insoluble in dichloromethane or chloroform. See ref 3a.