Comparative Investigation of Peripheral and Nonperipheral Zinc Phthalocyanine-Based Polycarbazoles in Terms of Optical, Electrical, and Sensing Properties

Abstract

In this study, nonperipherally alkyl-linked carbazole conjugated novel zinc(II) phthalocyanine was synthesized by cyclotetramerization reaction of 6-(9 H-carbazol-9-yl)hexane-1-thiol and 3,6-bis(tosyloxy) phthalonitrile in a one-step reaction. Optical, electrical, and sensing properties of this super structured polycarbazole obtained by electropolymerization are compared with peripherally alkyl-linked polycarbazole-based zinc(II) phthalocyanine. It has been found that the attachment of alkyl-linked carbazoles to the phthalocyanine molecule in either peripheral or nonperipheral positions has a great effect on the optical and electrical properties and sensing ability of the resulting polycarbazole derivatives. P(n-ZnPc) has the highest electrochromic contrast (70.5%) among the derivatives of zinc(II) phthalocyanines in the literature. In addition to these, the sensor platform has been successfully established, and analytical optimizations have been carried out. When the sensors prepared with zinc(II) phthalocyanine are examined, it was specified that the n-ZnPc- co-TP/GOx was ranked first in the literature with high sensor response and stability. As a result, by changing of the peripheral and nonperipheral position of phthalocyanines, their physical properties can be tuned to meet the requirements of desired technological application.

Investigation of polycarbazoles thin films prepared by electrochemical oxidation of 3- and 9-substituted carbazoles

“…But 9H-carbazole can also be substituted or polymerized either at the 3-and 6-positions or 2-and 7-positions to yield polycarbazole derivatives with good photoactive and electroactive properties due to their high hole transporting mobility and strong absorption in the UV region [24][25][26][27]. Due to these characteristics, polycarbazole derivatives are very interesting for applications such as light emitting diodes [28,29], transistors [30], photovoltaic devices [31,32], and (bio)sensors [33][34][35][36]. Polycarbazoles can be obtained either by chemical polymerization of carbazole in the presence of an oxidizing agent, such as ferric chloride, as first evidenced by Branch and Tucker [37,38], or by electrochemical polymerization leading to a thin film at the surface of a conducting electrode as first described by Ambrose and Nelson [39,40].…”

Hybrid Functional Analysis of Electronic Properties of Transition-Metal Phthalocyanines

“…Beside the light conversation and light emitting devices [13][14][15] including the photodynamic therapy [16,17], phthalocyanine are widely studied in the field of organic field transistors [18], gas sensors [19], and biosensors [20,21].…”

In Situ Electrochemical Production of Metal‐organic Hybrid Composite Film from Nickel Containing Polyoxometalate and 3,4‐Ethylenedioxy‐thiophene for Sensor Application

“…In recent years, the integration of inorganic species and CPs has led to the emergence of novel promising functional materials [12–16]. Among these materials, metal‐based CPs have been used in application of recent developments.…”