Design of novel substituted phthalocyanines; synthesis and fluorescence, DFT, photovoltaic properties

Abstract

The 4-(2-(3,4-dimethoxyphenoxy) phenoxy) phthalonitrile was synthesized as the starting material of new syntheses. Zinc, copper, and cobalt phthalocyanines were achieved by reaction of starting compound with Zn(CH3COO)2, CuCl2 and CoCl2 metal salts. Basic spectroscopic methods such as nuclear magnetic resonance electronic 2 absorption, mass and infrared were used in the structure characterization of the compounds. Absorption, excitation and emission measurements of fluorescence zinc phthalocyanine compound were also investigated in THF. Then, structural, energy and electronic properties for synthesized metallophthalocyanines were determined by quantum chemical calculations including DFT method. The band gap of HOMO and LUMO was determined to be chemically active. Global reactivity (I, A, η, s, μ, χ, ω) and non-linear properties were studied. In addition, molecular electrostatic potential (MEP) maps were drawn to identify potential reactive regions of metallo phthalocyanine (M-Pc) compounds. Photovoltaic performances of phthalocyanine compounds for dye sensitive solar cells were investigated. Solar conversion efficiency of DSSC based on copper, zinc and cobalt phthalocyanine compounds was 1.69%, 1.35% and 1.54%, respectively. Compounds have good solubility and show nonlinear optical properties. Zinc phthalocyanine gave fluorescence emission.

Solar energy conversion using first row d-block metal coordination compound sensitizers and redox mediators

“…A number of functionalized CuPc dyes in DSCs has been reported, with the degree of dye aggregation being a focus of attention. [224][225][226][227][228] For dyes containing carboxylic acid-functionalized porphyrin domains, the nature of the carboxylic acid linker has a noteworthy impact on the performance of DSCs. In 2010, Grätzel and coworkers investigated the photoconversion efficiencies of DSCs sensitized with CPICu and CPIZn (H 2 CPI, Scheme 22) and using an I 3 À /I À redox shuttle.…”

Effect of detonation nanodiamonds on the electrocatalytic activity of asymmetric cobalt phthalocyanine: Covalent versus non‐covalent linking

“…The syntheses of 4‐(benzo[d]thiazol‐2‐ylthio) benzene‐1,2‐dinitrile ( 1 ) and 4‐(carboxyethylsulphanyl) phthalonitrile ( 2 ) have been reported [26, 27].…”

Theoretical Investigation of 1H and 13C NMR Spectra of Diethanol Amine Dithiocarbamate RAFT Agent

“…Optimized structural parameters calculated with the DFT/B3LYP/6-311G and B3PW91/SDD basis set (Solğun et al 2020;Cabir et al 2020). The optimized molecular, bond lengths and bond angles between particles were compared with each other utilizing the two strategies are listed in Table 3.…”

“…The fundamental electronic parameters related to orbitals in a particle are the most elevated and possessed atomic orbital (HOMO) and the least abandoned atomic orbital (LUMO) and their energy gap (Janeoo et al 2022). HOMO are electrons within the furthest (most noteworthy vitality) orbital that can act as an electron donor (Ağırtaş et al 2020). The LUMO is the deepest (least vitality) orbital that has sufficient space to acknowledge electrons and can act as an electron acceptor (Solğun, Yıldıko, and Ağırtaş 2021).…”