The impact of [1,2,5]chalcogenazolo[3,4‐f]‐benzo[1,2,3]triazole structure on the optoelectronic properties of conjugated polymers

Abstract

Two novel conjugated near‐infrared (NIR) absorbing donor–acceptor type copolymers comprising benzodithiophene as the donor and [1,2,5]chalcogenazolo[3,4‐f]‐benzo[1,2,3]triazole derivatives as the acceptors, spaced with thiophene as the π‐bridge, were designed and synthesized via Stille polycondensation reaction. The effect of acceptor strength on optoelectronic properties was targeted and investigated. Branched alkyl chains (the extended 2‐octyl‐1‐dodecyl alkyl chain; C8C12) were introduced to 5H‐[1,2,3]triazolo[4′,5′:4,5]benzo[1,2‐c][1,2,5]thiadiazole and 5H‐[1,2,3]triazolo[4′,5′:4,5]benzo[1,2‐c][1,2,5]selenadiazole for enhanced solubility of polymers which ease the processability hence device constructions. The strongly electron‐withdrawing units lead to a substantial change in the absorption properties via promotion of the intramolecular charge transfer band alongside the π–π* transition. The resultant soluble polymers were characterized via cyclic voltammetry to determine highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels as −5.00 and −3.92 eV for PSBT and −4.86 and −4.04 eV for PSeBT, respectively. Electronic band gaps of the copolymers were calculated as 1.08 eV for PSBT and 0.82 eV for PSeBT, respectively. NIR absorbing copolymers were used to construct electrochromic devices.

Construction of amperometric biosensor modified with conducting polymer/carbon dots for the analysis of catechol

“…Density functional theory (DFT) calculations were performed by using the B3LYP/6‐311G*hybrid functional 30–32 and basis set, using 10 −8 RMS density matrix convergence and 10 −6 energy change criteria in Gaussian09 (Revision A.02) 33 . Successful results were achieved previously at this level of calculations for donor‐acceptor studies in the literature 34,35 . Results are validated by novel and promising TPSSh functional 36 .…”

“…33 Successful results were achieved previously at this level of calculations for donor-acceptor studies in the literature. 34,35 Results are validated by novel and promising TPSSh functional. 36 HOMO, LUMO, electrostatic potential surfaces (ESP), counterpoise corrected interaction energy of PFTBDT with catechol and effect of catechol on the electronic structure such as charge transfer were calculated for the geometry optimized structures of tetramer model oligomers with methyl side chains.…”

Side chain effect on the electrochemical and optical properties of thieno[3,4-c]pyrrole-4,6-dione based donor–acceptor donor type monomers and polymers

“…ProDOT with the didecyl substitution was also constructed to determine the effect by using B3LYP hybrid functional and 6-311G(d) basis set with tight SCF convergence criteria in the Gaussian09 (Revision A.02) software package, which provided successful results in the previous studies. [41][42][43][44][45][46][47][48] Geometry optimizations were started from different initial conformations by controlling the torsional angle between connected donor, bridge and acceptor units to determine the lowest energy geometry. The optimized geometries were utilized for the calculation of electrostatic potential surface (ESP), the highest occupied molecular orbitals (HOMO), and the lowest unoccupied molecular orbitals (LUMO).…”

Multistage Responsive Materials for Real‐time, Reversible, and Sustainable Light‐Writing

“…The color of red (Δa > 0) and blue (Δb < 0) became stronger which is consistent with the result of fluorescence spectra (more details are given in Table S1, Supporting Information). [58,59] The well-organized multistage responsive behaviors, especially the significant polarity-related fluorescence response, make the materials an ideal real-time noncontact writing material.…”