Thieno[3,2-b]thiophene and triphenylamine-based hole transport materials for perovskite solar cells

Abstract

Heterocyclic compounds have played significant roles in achieving high performance as hole transport materials (HTMs) for perovskite solar cell (PSC) applications. Various studies have focused on the development of fused heterocyclic conjugated structures for hole transport materials. In this report, three novel π-extended conjugated materials (M1-M3), based on thieno[3,2-b]thiophene (TT) and 4,4′-dimethoxytriphenylamine [TPA(OMe)2], were designed and successfully synthesized via Palladium (0) catalyzed Suzuki coupling reaction. Their optical, electrochemical, and thermal properties were investigated by UV-Vis, fluorescence, cyclic voltammetry, and thermal analysis. The materials were utilized as hole transport materials in p-i-n architecture perovskite solar cells, which displayed performances of open-circuit voltage (Voc) as high as 1,050 mV, a maximum short-circuit current (Jsc) of 16,9 mA/cm2, a maximum fill factor (FF) of 29.3%, and a power conversion efficiency (PCE) of 5.20%. This work demonstrated that thieno[3,2-b]thiophene and TPA(OMe)2-based structures are promising cores for high-performance hole transport materials in perovskite solar cell architecture.

High-Performance Thienothiophene and Single Wall Carbon Nanotube-Based Supercapacitor as a Free-Standing and Flexible Hybrid Energy Storage Material

“…Thieno­[3,2- b ]­thiophene (TT) has a rigid structure with extended π-conjugation, which makes it suitable π-linker for adjusting the band gap of organic materials and to increase the intermolecular interactions in solid state. − It is an electron-rich molecule, making it a promising material for the construction of conjugatedlow band gap polymeric semiconductors for energy-based applications such as organic solar cells, organic light-emitting diodes, and organic field-effect transistors. − In this report, we describe supercapacitor and energy storage performances of TT-TPA-SWCNT by cyclic voltammetry (CV), galvanostatic charge/discharge (GCD), and electrochemical impedance spectroscopy (EIS). For the first time, a high-performance free-standing and flexible electrode, based on a thienothiophene (TT) derivative and SWCNT, prepared without using any nonconductive binding agent, is reported.…”

A multifunctional thienothiophene member: 4-thieno[3,2-b]thiophen-3-ylbenzonitrile (4-CNPhTT)

“…This method has now been used by some groups and declared as a convenient method, with the synthesis being performed via alternative synthetic routes, simplifying the variation of the side chains of the outer thiophene site with a universal TT building block that can be produced with good yields from inexpensive starting materials [ 29 – 31 ]. Such substitutions caused remarkable changes in the electronic and optical properties of polymeric and small molecules constructed using TTs as building blocks [ 32 – 39 ].…”

Thienothiophene-based organic light-emitting diode: synthesis, photophysical properties and application

“…These compounds are electron-rich, flat and electron-delocalized systems, properties that make them promising materials for the construction of Scheme 1: Synthesis of DMB-TT-TPA (8). conjugated energy-based semiconductors for OLEDs [20][21][22][23], perovskite solar cells [24,25], organic field-effect transistors (OFETs) [26][27][28], capacitors [29,30], hybrid films [31], and photosensitizers [32][33][34]. Another important π-conjugated unit is triphenylamine (TPA), having an ionization potential of 6.80 eV, which is lower compared to many other organic cores, thus providing a strong electron-donating ability for organic electronic applications [12,35].…”