Copolymers of 4‐thieno[3,2‐b]thiophen‐3‐ylbenzonitrile with anthracene and biphenyl; synthesis, characterization, electronic, optical, and thermal properties

Abstract

Two novel copolymers of 4-thieno[3,2-b]thiophen-3-ylbenzonitrile (TT-CN), possessing electron withdrawing cyano moiety, with anthracene (P1) and biphenyl (P2) were prepared via Suzuki coupling. Optic, electronic, and thermal properties of the copolymers were investigated through UV-Vis spectroscopy, cyclic voltammetry, gel permeation chromatography, and thermal gravimetric analysis. The polymers with anthracene and biphenyl had electronic band gaps of 2.01 and 1.90 eV, respectively. Both polymers demonstrated excellent large Stokes shifts of 101 (anthracene) and 105 nm (biphenyl) as well as very good thermal properties. As they had good optical, electronic, and thermal properties, they are promising candidates for electronic applications.

Triphenylamine/4,4′-Dimethoxytriphenylamine-Functionalized Thieno[3,2-b]thiophene Fluorophores with a High Quantum Efficiency: Synthesis and Photophysical Properties

“…The monoketones ( 1a–e ), TTs ( 2a–e ), some of the brominated TTs ( 3a, 3c, 3d ), and TT-TPA derivatives (4a, 4c, 4d) were synthesized following our previous reports. − The reaction of 3-bromothiophene with n- butyllithium at −78 °C was followed by the addition of elemental sulfur and then α haloketones to produce 1a–e in 84, 81, 79, 88, and 82% yields, respectively. Their ring closure reactions were conducted in the presence of polyphosphoric acid (PPA) in refluxing chlorobenzene to give 2a–e in 69, 85, 79, 94, and 83% yields, respectively.…”

“…An important advantage is that fluorescence properties can be finely tuned through chemical modification of their structures. − In particular, the geometrical design and conformation of the fluorophores have a crucial influence on their fluorescence and electroluminescence properties. − Thiophene-derived conjugated compounds, such as thienothiophenes (TTs), have particular importance as they are easy to modify in addition to their electron-rich, flat, and good electron delocalized structures. Thus, they are widely used in optoelectronic applications owing to their notable optic, electronic, and redox properties. − …”

A Review on Solution-Processed Organic Phototransistors and Their Recent Developments

“…Substituent effect and bridging atoms effect are other effective strategies for tailoring energy levels of polymers [115]. Recently, copolymers of 4-thieno[3,2-b]thiophen-3-ylbenzonitrile with anthracene (P1) and biphenyl (P2) were synthesised and characterised for optical, electronic and thermal properties [116]. These two novel copolymers were found promising OSC choices in electronic applications due to their low bandgaps (2.01, eV and 1.9 eV, respectively).…”

A Review on Solution-Processed Organic Phototransistors and Their Recent Developments

“…In Figure 13, the chemical structures of some small molecules and polymers used in OPT device are shown. b]thiophen-3-ylbenzonitrile with anthracene (P1) and biphenyl (P2) were synthesised and characterised for optical, electronic and thermal properties [116]. These two novel copolymers were found promising OSC choices in electronic applications due to their low bandgaps (2.01, eV and 1.9 eV, respectively).…”