Synthesis and electrochemical characterization of new linear conjugated arylamine copolymers

Abstract

New conjugated copolymers having linear structures were synthesized by palladium catalyzed cross-coupling reactions of bis(4-bromophenyl)phenylamine or 4-hydroxymethyl-N,N’-bis(4-bromophenyl)aniline and two bisboronic acids of fluorene or thiophene. The copolymers were obtained as fully or partially soluble materials, in chlorinated and aprotic polar solvents. Having a hydroxymethyl group attached to the para position of the triphenylamine units, the synthesized copolymers can be viewed as functional polymers which were transformed into new ones by employing suitable chemical reactions. A new copolymer was obtained by coupling the hydroxymethyl group of triphenylamine of P35 copolymer, with phenyl isocyanate. The chemical structures and the properties of copolymers were investigated by spectroscopic methods such as 1H nuclear magnetic resonance, Fourier transform infrared, ultraviolet-Vis and photoluminescence spectroscopy. Cyclic voltammetry was performed in order to obtain information about the electrochemical stability and reversibility of the redox processes of copolymers. Electrochemical studies were carried out on films cast on glassy carbon electrode (GCE) or In-Tin oxide (ITO) glass-coated electrode.

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

“…4-Formyl triphenylamine [22] and 4,4′,4′′-triformyl triphenylamine [23–25] were obtained by formylation of TPA according to the reported methods. 4-Formyl-N,N′-bis(4-bromophenyl) aniline [26], tris (4-iodophenyl) amine [27] and vinyl triphenylamine [28] were synthesized and purified according to the literature procedures. 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.…”

Synthesis and Properties of an Electropolymer Obtained from a Dimeric Donor/Acceptor System with a 4,4′-Spirobi[cyclopenta[2,1-b:3,4-b′]dithiophene] Core

“…Instrumentation. 1 H and 13 C NMR spectra were recorded on a Bruker Avance 400 (400 and 100.6 MHz, respectively); chemical shifts are indicated in parts per million downfield from SiMe 4 , using the residual proton (CHCl 3 = 7.26 ppm) and carbon (CDCl 3 = 77.0 ppm) solvent resonances as the internal reference. Coupling constant values J are given in Hz.…”

“…1 H NMR (CDCl 3 , 400 MHz): δ 9.69 (s, 2H), 7.27−7.23 (s, 12H), 7.21 (s, 2H), 7.1−7.08 (m, 8H), 7.06−7.02 (m, 4H), 7.00 (d, J = 8.8 Hz, 4H), 6.92 (m, 4H), 6.55 (s, 2H). 13 …”

“…1 16.0 Hz, 2H), 6.54 (d, J = 4.9 Hz, 2H), 6.50 (s, 2H). 13 2,2′-Diformyl-6,6′-bis-[(E)-(4-diphenylaminostyryl)]-4,4′-spirobi-[cyclopenta[2,1-b:3,4-b′]dithiophene] (4). In a flame-dried two necked round-bottom flask equipped with a reflux condenser and a magnetic stirrer compound 3 (126 mg, 0.14 mmol) was dissolved under an inert atmosphere in dry 1,2-dichloroethane (DCE, 7 mL).…”

“…In the past years we developed polymeric materials, produced by electrochemical methods, where both donor and acceptor groups, linked by a conjugated backbone, were already present in the structural monomer. [9][10][11][12][13][14]21,22 These materials exhibited photovoltaic and electrochromic properties [9][10][11][12][13][14]21 and were applicable in the construction of an electroluminescent device. 22 In all cases, monomers holding the spiro configuration were selected.…”