New metallophthalocyanines including benzylphenoxy groups and investigation of their organic-field effect transistor (OFET) features

• Published in: Dyes and pigments 2022-04, Vol.200, p.110125, Article 110125
• Main Authors: Özdemir, Mücahit, Altinisik, Sinem, Köksoy, Baybars, Canımkurbey, Betül, Koyuncu, Sermet, Durmuş, Mahmut, Bulut, Mustafa, Yalçın, Bahattin
• Format: Article
• Language: English
• Subjects: DFT; Electrochemistry; OFET; Phthalocyanine; Synthesis
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2022.110125

In this study, metal and metal-free novel phthalocyanines containing peripheral and non-peripheral tetra 2-benzylphenoxy groups were synthesized. The compounds were characterized by UV–Vis, FT-IR, 1H NMR, and MALDI-TOF mass spectrometry as well as elemental analysis. These new phthalocyanines exhibited excellent solubility in most organic solvents, and their redox behavior was investigated in different solvents such as dimethyl sulfoxide (DMSO) and dichloromethane (DCM). The redox behavior of the peripheral and non-peripheral phthalocyanine compounds 1a-c and 2a-c was determined by cyclic voltammetry and in situ spectroelectrochemistry. According to organic field-effect transistors (OFETs) measurements, the peripheral and non-peripheral phthalocyanine-cobalt complexes which have higher mobility than others were utilized top-gate bottom-contact OFETs fabrication. The output characteristics of the device show that its mobility is approximately 5 × 10−2 cm2/Vs with p-type accumulation. This study provides synthesis, characterization, electrochemical properties, surface analysis, DFT and OFET properties of copper(II), nickel(II) and cobalt(II) phthalocyanine derivatives. [Display omitted] •Synthesis and characterization of alpha and beta metallo phthalocyanines containing 2-benzylphenoxy.•The synthesized phthalocyanines were characterized by elemental analysis, UV–Vis, FT-IR, 1H NMR, and MALDI-TOF-MS.•TEM and AFM imaging of the copper, nickel and cobalt phthalocyanine films.•Theoretical, optical and electrochemical measurements of the phthalocyanines.•Organic field-effect transistors measurements of the peripheral and nonperipheral phthalocyanines.