Synthesis of phenothiazine derivatives as novel moieties toward utilization in alternative donor – acceptor conjugated polymers

Two new phenothiazine – based structures, including 4-(10H-phenothiazin-10-yl)-N,Ndiphenylaniline (PDA) and 10-(pyren-1-yl)-10H-phenothiazine (PyP) were synthesized via Buchwald-Hartwig C-N coupling amination using catalytic palladium modulated by electronrich ligands. | Vietnam Journal of Science and Technology 56 (3B) (2018) 177-183 SYNTHESIS OF PHENOTHIAZINE DERIVATIVES AS NOVEL MOIETIES TOWARD UTILIZATION IN ALTERNATIVE DONOR – ACCEPTOR CONJUGATED POLYMERS Truong Tung Khuong1, Nguyen Tran Ha1, *, Le Anh Kien2 1 Faculty of Materials Technology, Ho Chi Minh City University of Technology, Vietnam National University, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City 2 Tropical Environmental Institute, 57 Truong Quoc Dung, Phu Nhuan District, Ho Chí Minh City * Email: nguyentranha@ Received: July 13, 2018; Accepted for publication: xxx, 2018 ABSTRACT Two new phenothiazine – based structures, including 4-(10H-phenothiazin-10-yl)-N,Ndiphenylaniline (PDA) and 10-(pyren-1-yl)-10H-phenothiazine (PyP) were synthesized via Buchwald-Hartwig C-N coupling amination using catalytic palladium modulated by electronrich ligands. Chemical structures were analysed via proton nuclear magnetic resonance (1H NMR) spectroscopy. Then, photo-properties were characterized by UV – Vis absorption spectroscopy in various concentrations of each product. The results showed that PDA and PyP are highly potential donor units for well-performed donor – acceptor conjugated polymers. Keywords: C-N coupling, Buchwald-Hartwig amination, phenothiazine – based structures, donor units. 1. INTRODUCTION Since Alan J. Heeger, Alan G. MacDiarmid and Hideki Shirakawa were awarded jointly the Nobel Prize in Chemistry 2000 for their discovery and development of conductive polymers, conjugated polymers have been attracting great concern from scientists as well as businesses thanks to their widespread applications in a broad range of fields. Among the various types of this materials that have been researched and developed for the many years the donor – acceptor conjugated polymers (D – A CPs) with its distinctive structure have offered a large variety of applications, especially in the field of flexible electronic applications. The most noticeable point in the .

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