Synthesis and Optoelectronic Properties of Alternating Copolymers Containing Anthracene Unit in The Main Chain by Radical Ring-Opening Polymerization

Abstract

Novel alternating copolymers composed of anthracene moiety and halostyrene unit were synthesized by ring-opening polymerization of cyclic monomers, 10-methylene-9,10-dihydroanthryl-9-spirop-chlorophenylcyclopropane and its bromo derivative. Reversible addition-fragmentation chain transfer and conventional free radical polymerizations were employed for the purpose. In both cases, the ring-opening polymerization proceeded predominantly to afford alternating copolymer containing anthracene unit in the main chain. Incorporations of optoelectronic groups, involving diphenylamine, carbazole, and phenothiazine, on the halostyrene moieties of the alternating copolymers were conducted by palladium-catalyzed reactions. Novel nonconjugated copolymers having perfect alternating structures were obtained, in which the alternate arrangement of two distinct electronic functionalities is formed owing to the ring-opening polymerization system. Resulting anthracene-based alternating copolymers having two distinct electronic functionalities exhibited characteristic fluorescence resonance energy transfer, as confirmed by UV-vis and fluorescence spectra.

Living Radical Polymerization by the RAFT Process – A Third Update

“…A [285] BA [285] St [285] 54 S S * St [132,286] PFPVS [169] PVS [169] 381 [287] (382) [287] 414 [288] BA [286] 364 [289] (VAc) [274] (NVP) [248] (NES) [290] (BES) [290] MAA/EGDMA [291] (PFPVS-b-PS) [169] (399-b-EA) [288] 364-b-387 [289] 55 S S * tBA [292] 368 [292] tBA-b-368 [292] (Continued ) [293] St [293] 57 S S N * iBoA [268,[294][295][296] 351 [297] St [298] 58…”

“…[440] RAFT polymerization with xanthate (229) was controlled although dispersities were broad. [113,506] This was attributed to the low transfer 373 [469] 378 [347] 379 [347] 386 [413] 387 [289] 391 [465] 392 [434] 393 [451] 388 [538] 389 [583] 390 [395] 380 [433] 383 [470] 384 [470,471] 385 [433] 374 [469] 375 [469] 381 [287] 382 [287] 376 [347,433] 377 [412] Fig. 9.…”

Simultaneous Control over Monomer Sequence and Molecular Weight Using the RAFT Process

“…An example is presented by Mori and coworkers, who reported the radical ring-opening polymerization of 10-methylene-9,10-dihydroanthryl-9-spirophenylcyclopropane, as well as its p-bromo, p-chloro and pyridine derivatives, which could be controlled with RAFT (68,69). The resulting polymer contains alternating sequences of anthracene and styrene (derived) moieties ( Figure 5).…”

Formal aryne/ethylene copolymerization to form polyethylene containing o-arylene units in the main chain

“…(In this manuscript, chain-growth polymerization of monomers bearing a preformed arylene unit is excluded. For example, see Bunz et al 1 ) In this regard, various polymerization methods have been developed for the introduction of para-arylene units, including the polymerization of p-quinodimethanes 2 or their surrogates, 3,4 the polymerization of p-arylene equivalents, [5][6][7][8] and the catalyst-transfer chain-growth condensation polymerization of bifunctional monomers. [9][10][11] However, fewer methods have been developed for the synthesis of meta-arylene units [12][13][14][15] and ortho-arylene units.…”