Synthesis and Characterization of Star Copolymers Consisting of Fullerene and Conjugated Polyphenylene:  6-star-C₆₀[styrene−poly(1,4-phenylene)-block-polystyrene] and 6-star-C₆₀[polystyrene-block-poly(1,4-phenylene)]

Abstract

The grafting of "living" polystyrene-block-poly(1,3-cyclohexadiene)-block-styryllithium and poly(1,3-cylclohexadiene)-block-polystyryllithium onto C 60 yielded, respectively, 6-star-fullerene[styreneblock-poly(1,3-cyclohexadiene)-block-polystyrene] and 6-star-fullerene[polystyrene-block-poly(1,3-cyclohexadiene)]. Selective dehydrogenation of these macromolecules yielded, respectively, 6-star-fullerene-[styrene-block-poly(1,4-phenylene)-block-polystyrene], C60(st-PPP-PS)6, and 6-star-fullerene [polystyreneblock-poly(1,4-phenylene)], C60(PS-PPP)6. 6-star-Fullerene[poly(1,4-phenylene)-block-polystyrene] could not be synthesized via this route as fullerene-poly(1,3-cyclohexadiene) bonds were found to form without control and to degrade during aromatization. Star copolymers containing conjugated PPP were characterized by size exclusion chromatography, UV, and fluorescence spectroscopy. Fluorescence quantum yields of C 60(st-PPP-PS)6 and C60(PS-PPP)6 in THF were compared and discussed in light of characterizations of PPP-PS-PPP in comparable conditions without or mixed with C60(PS)6.

Kinetics of Fullerene (C60) Inhibition in Polymerization of Vinyl Acetate (VA) Using Bismuthonium Ylide as Initiator

“…Fullerene (C 60 ), due to its unique properties [1,2], has applications in different fields such as pharmaceuticals [3], automobiles [4], preparation of fullerene-based polymers [5][6][7] and co-polymers [8][9][10]. Fullerene-containing polymeric materials have novel optical [11][12][13] and electro active properties [14][15][16][17][18] and have been used in organic solar cells [19,20].…”

Ultrasound‐accelerated dehydrogenation of poly(1,3‐cyclohexadiene): efficient synthesis of poly(para‐phenylene)

“…Accordingly, a variety of different approaches have been attempted to improve the solubility of PPP. Ultimately, the most promising route to obtain soluble PPP is the dehydrogenation of poly(1,3‐cyclohexadiene) (PCHD) and its derivatives (Scheme ) 7–30. Therefore, various polymerization and dehydrogenation reactions for PCHD have been examined.…”

“…Therefore, various polymerization and dehydrogenation reactions for PCHD have been examined. As a result, the dehydrogenation of anionically polymerized PCHD with benzoquinones has been found to be one of the most effective methods to synthesize soluble PPP 10–30. However, although a high conversion of cyclohexadiene (CHD) units to phenylene (Ph) units can be achieved by the dehydrogenation of PCHD with benzoquinones, a long reaction time and/or a high reaction temperature are always required.…”

Degradation of the covalent carbon–carbon bond between fullerene‐C60 and poly(1,3‐cyclohexadiene)

“…The synthesis of fullerene‐C 60 (C 60 ) end‐capped polymers (C 60 ‐polymers) is one of the most interesting subjects in basic polymer research and is a practical method to obtain new functional materials for a wide range of applications. For example, C 60 ‐polystyrene (C 60 ‐PSt), 1 C 60 ‐polyisoprene (C 60 ‐PIp),1 C 60 ‐PIp‐PSt block copolymer (C 60 ‐PIp‐PSt),2 C 60 ‐PSt‐poly(1,3‐cyclohexadiene) (PCHD) block copolymer (C 60 ‐PSt‐PCHD),3 C 60 ‐PCHD,4 C 60 ‐poly( N ‐vinylcarbazole) (C 60 ‐PNVC),5 and C 60 ‐poly(4‐diphenylaminostyrene) (C 60 ‐PDAS)6 were synthesized by the grafting reaction of polymer carbanions onto C 60 . Among the innumerable combinations of C 60 and polymers, C 60 ‐poly( para ‐phenylene) (C 60 ‐PPP) has been recognized as one of the most attractive structures, because excellent optical, electrical, and opto‐electrical properties are expected from this polymer.…”