Synthesis and properties of anthracene containing polyethers

Abstract

Four poly(oxymethyleneanthrylene)s were prepared by polycondensation of 9,10‐diacetoxyanthracene (and a substituted analogue) with α,ω‐dibromoalkanes. Two model compounds were also synthesized by the same procedure. Although non‐conjugated the polymers could be doped with iodine. The redox reaction of doping was confirmed by the changes in the electronic and fluorescence spectra as well as by the appearance of paramagnetism and enhanced electrical conductivity. In comparison, the model compounds could not be doped. Doping with iodine occurs only when the polymers are in the solid state. This solid state polymer effect, reported also in previous publications, is explained by collective interactions of several anthracene units with the dopant.

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

“…In addition to anthracene-based conjugated polymers, increasing attention has been recently paid to nonconjugated polymers with anthracene units in the main chain, such as poly-(trimethyleneanthrylene)s, 8,9 poly(octamethyleneanthrylene)s, 10 and poly(9,10-oxymethyleneanthrylene)s. 11 Nonconjugated polymer having anthracene units linked in the 9,10-position with flexible alkyl chains was reported to afford paramagnetism by doping with iodine and enhanced electrical conductivity. 11 Various polyamides, 12,13 polyesters, 14,15 polyethers, 14 and polyurethanes 13 containing anthracene units in the main chain have been synthesized by several groups. Much attention has been also paid to anthracene-based polymers and molecules having an additional optoelectronic component, such as triphenylamine, [16][17][18][19] carbazole, [20][21][22] and phenothiazine, 23,24 because the combination of two distinct electronic functionalities in a single system provides a great variety of photophysical and optoelectronic properties.…”

Polymers Composed of Alternating Anthracene and Pyridine Containing Units by Radical Ring-Opening Polymerization: Controlled Synthesis, Optical Properties, and Metal Complexes

“…Furthermore, the anthracene-based nonconjugated polymers afforded paramagnetism by doping with iodine and enhanced electrical conductivity. 14 Various polyamides, 15,16 polyesters, 17,18 polyethers, 17 and polyurethanes 16 containing anthracene units in the main chain have been synthesized so far. On the other hand, the control of their molecular weights, polydispersity, composition, and polymer structure is difficult because these polymers are synthesized by stepwise polymerization.…”

“…Anthracene-containing polymers have attracted significant research interest, due to their promising features as fluorescent labels, photon harvesters, and optoelectronic applications (e.g., organic light emitting diodes, organic field-effect transistors, photovoltaics). − Among them, conjugated polymers containing anthracene units in the main chain can be readily modified to optimize their optoelectronic properties by adjusting the polymer structure (e.g., the elongation of conjugated bonding, incorporation of substituent groups into the anthracene unit, and so on), potentially bringing in the advantages for the optoelectronic applications. − In addition to the large variety of anthracene-based conjugated polymers, nonconjugated polymers with anthracene units in the main chain linked at the 9,10-positions with flexible alkyl chains, such as poly(trimethyleneanthrylene)s, , poly(octamethyleneanthrylene)s, and poly(9,10-oxymethyleneanthrylene)s, have been reported as well. Furthermore, the anthracene-based nonconjugated polymers afforded paramagnetism by doping with iodine and enhanced electrical conductivity .…”

“…Anthracene-containing polymers have attracted significant research interest, due to their promising features as fluorescent labels, photon harvesters, and optoelectronic applications (e.g., organic light emitting diodes, organic field-effect transistors, photovoltaics). − Among them, conjugated polymers containing anthracene units in the main chain can be readily modified to optimize their optoelectronic properties by adjusting the polymer structure (e.g., the elongation of conjugated bonding, incorporation of substituent groups into the anthracene unit, and so on), potentially bringing in the advantages for the optoelectronic applications. − In addition to the large variety of anthracene-based conjugated polymers, nonconjugated polymers with anthracene units in the main chain linked at the 9,10-positions with flexible alkyl chains, such as poly(trimethyleneanthrylene)s, , poly(octamethyleneanthrylene)s, and poly(9,10-oxymethyleneanthrylene)s, have been reported as well. Furthermore, the anthracene-based nonconjugated polymers afforded paramagnetism by doping with iodine and enhanced electrical conductivity . Various polyamides, , polyesters, , polyethers, and polyurethanes containing anthracene units in the main chain have been synthesized so far.…”

Synthesis, Assembled Structures, and Optoelectronic Properties of Amphiphilic Block Copolymers Containing Anthracene Units in the Main Chain

“…Anthracene‐containing polymers have attracted significant research interest, because of their attractive features as fluorescent labels, photon harvesters, and electro‐ and photoluminescent materials. In addition to conjugated polymers with anthracene units in the main chains, such as poly(anthrylene)s,9, 10 poly(anthrylenevinylene) s,11–13 and poly(anthryleneethynylene)s,14, 15 considerable interest has been devoted to non‐conjugated polymers, in which the anthracene units are linked in the 9,10‐position with flexible alkyl chains 16–19. In contrast, various block copolymers having anthracene moieties in the side chain have been recently synthesized by controlled radical polymerization methods 20–23.…”