Indolo[3,2‐b]carbazole‐based poly(arylene vinylene)s. The influence of substitution position on spectroscopic and electrochemical properties

Abstract

Three novel soluble poly(arylene vinylene)s containing indolo[3,2-b]carbazole moiety inserted in the polymer chain at 2,8-, 3,9-and 6,12-positions were synthesized and used to study the influence of the linking topology on the optical and electronic properties. The new polymers were obtained through a palladium-catalysed cross-coupling Stille reaction between bis-bromine[3,2-b]indolocarbazoles and trans-1,2-bis(tributylstannyl)ethane in toluene.Polymers were soluble in chlorinated, aromatic and aprotic polar solvents. The structures of polymers were investigated using Fourier transform infrared, 1 H NMR and 13 C NMR spectroscopies. The number-average molecular weights determined using gel permeation chromatography are in the range (6.3-9.4) × 10 3 g mol −1 while thermogravimetric analysis showed the polymers to possess high thermal stability. UV-visible and emission spectroscopy evidenced a bathochromic shift of max for indolocarbazole linking topology in the polymer backbone, in the order: 6,12 < 2,8 < 3,9. Electrochemical properties were investigated by cyclic voltammetry using thin films cast on platinum disc working electrodes and highest occupied and lowest unoccupied molecular orbital energy levels were determined.

Aggregate emission behaviors and reversible mechanofluorochromic properties of α-cyanostilbene functionalized indolo[3,2-b]carbazole derivatives

“…Compound ICZBr was synthesized according to the literature. 7 ICZCHO was synthesized via the Suzuki-Miyaura cross-coupling reaction, using (4-formylphenyl)boronic acid in tetrahydrofuran-water mixture solution. The target compounds were obtained by the Knoevenagel condensation reaction with satisfactory yields, using the benzyl cyanide derivatives in ethanol solution.…”

Indolo[3,2‐b]carbazole‐based poly(arylene ethynylene)s through Sonogashira coupling for optoelectronic and sensing applications

“…Fused aromatic and heteroaromatic ring containing compounds have by now gained significant attention due to their extensive applications in advanced electronic and optoelectronic devices . The 5,11‐dihydroindolo[3,2‐b] carbazoles (ICZs) have a ladder type planar structure similar to pentacenes .…”

“…The 5,11‐dihydroindolo[3,2‐b] carbazoles (ICZs) have a ladder type planar structure similar to pentacenes . They have gained significant technological interest in recent years due to many interesting applications in organic electronics . The two nitrogen atoms in ICZs are ex situ to each other in the carbazole fragment yielding an electron‐donating character, rigid and coplanar structure with a more extended conjugation, and higher charge carrier mobility compared to carbazole.…”

Molecular design of optoelectronic structures based on carbazole- and indolocarbazole-containing polyphenylquinolines

“…In succeeding years, the development of materials for optoelectronics was associated with a search for polyconjugated polymers. [13][14][15][16] In particular, polyphenylenevinylenes and polymers having donor moieties of indolo [3,2-b]carbazole (ICz), which have values of I D lower than that of carbazole (Cz), were synthesized. Cz and ICz were incorporated into both the side chain [17][18][19] and the backbone.…”

“…Cz and ICz were incorporated into both the side chain [17][18][19] and the backbone. 16,20 There are polymers that received attention because of having moieties of triphenylamine (TPA), which are introduced into the monomer unit. At that, the polymers synthesized have a structure similar to that of polyconjugated polymers as polyimides (PIs).…”