Synthesis of Soluble Poly(arylenevinylene)s Carrying Various Heterocycles as Arylene Units

Abstract

The Wittig reactions of 2,5-bis(dodecyloxy)-p-xylylenebis(triphenylphosphonium bromide) (6c) with thiophene-2,5-dicarbaldehyde (la), selenophene-2,5-dicarbaldehyde (lb), tellurophene-2,5dicarbaldehyde (lc), and benzo[c]thiophene-1,3-dicarbaldehyde (Id) were carried out to obtain poly(2,5thiophenediylvinylene-(7ac), 2,5-selenophenediylvinylene-(Tbc), 2,5-tellurophenediylvinylene-(7cc), and l,3-benzo[c]thiophenediylvinylene-aZi-2,5-bis(dodecyloxy)-l,4-phenylenevinylene)s (7dc), respectively. These polymers were characterized by NMR, IR, UV-vis, and elemental analysis. Their voltammetric and optical third-harmonic generation (THG) measurements were carried out.

Synthesis and Optoelectronic Characterization of Some Star-Shaped Oligomers with Benzene and Triphenylamine Cores

“…Triphenylphosphonium salts were also obtained in a series of chemical reactions in our laboratory, using the starting compounds: 1,3,5-tris (bromomethyl) benzene, N,N-dimethylaniline, and anthracene. 1,3,5-Tris (methylene-triphenyl phosphonium bromide) benzene was prepared as described in literature [29]. 4-(N,N-Dimethylamino)benzyl(triphenyl)phosphonium iodine was synthesized according to the reported procedure [30].…”

Polytellurophenes

“…[42] The reaction ( Figure 3) gives a red polymer in 65% yield that is soluble in both chloroform and THF. The polymer has an M n of 7.0 kg Á mol À1 , which was determined by GPC versus polystyrene standards.…”

Poly(dithienylethene‐alt‐1,4‐divinylenephenylene)s: Increasing the Molecular Weights in Diarylethene Photochromic Polymers

“…Unless otherwise specified, all reagents and catalysts were commercial (Aldrich). 1,2-Bis(2-methyl-3-thienyl)perfluorocyclopentene [5], 2,5-dihexyloxy-1,4-xylene bis(diethylphosphonate) [19,20] (2), and 2,5-bis(dodecyloxy)-1,4-xylylene bis(triphenylphosphonium bromide) [21] (3) were prepared according to literature procedures.…”

“…[14,16,26] In order to minimize the content of insoluble material we then synthesized an analogous dithienylethene-PPV copolymer via the Wittig reaction in tetrahydrofuran (THF) (see Scheme 2). [21] Since previous studies concerning the solubility of dialkyloxyxylene phosphonium salts have demonstrated that the hexyloxy derivative is only partially soluble in THF, we chose dodecyloxy groups as substituents in order to reach a complete solubility of the reagent 3 in the reaction medium. Following this procedure, poly(dithienylethene)-alt-didodecyloxyphenylenevinylene (poly-2) was obtained, with the yield of the soluble polymer rising from 3.3 % of poly-1 to 28 % of poly-2; no insoluble residue was formed.…”