Syntheses of novel fluorinated dibenzo[a,c]phenazine comprising polymers for electrochromic device applications

Hacioglu, Serife O.
Aktas, Ece
Hizalan, Gonul
Akbasoglu, Naime
Çırpan, Ali
Toppare, Levent Kamil
In this study, two novel fluorinated dibenzo[a,c]phenazine derivatives, 2,7-bis(5-bromo-4-hexylthiophen2-yl)-11-fluorodibenzo[a,c]phenazine (TFBPz) and 2,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-11- fluorodibenzo[a,c]phenazine (EFBPz), were synthesized by coupling fluorodibenzo[a,c]phenazine (FBPz) with electron rich 3-hexylthiophene and ethylene dioxythiophene (EDOT) units. The monomers were polymerized electrochemically and their electrochemical, spectroelectrochemical and electrochromic behaviors were studied. Then, PTFBPz and PEDOT comprising electrochromic device was constructed and reported. Comparing both polymers in terms of their redox potentials, as expected, PEFBPz showed a lower oxidation potential due to the insertion of an electron rich EDOT unit into the polymer chain, which increased the electron density significantly. EDOT comprising dibenzo[a,c]phenazine derivative PEFBPz exhibited a red shifted neutral state absorption with lower optical band gap values compared to those of PTFBPz. Furthermore, three novel D–A type dibenzo[a,c]phenazine comprising polymers (PBDT-TFBPz, PBDT-FBPz and PSi-TFBPz) were synthesized chemically and all polymers were investigated in terms of their electrochromic and physicochemical behaviors.


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In this study two donor-acceptor type alternating polymers containing electron-deficient benzotriazole moiety and electron-rich selenophene bearing benzodithiophene moiety; P1 and P2, were designed and synthesized via Stille polymerization. Moreover, the effects of thiophene and selenophene as pi-bridges on optical, electrochemical and optoelectronic features of polymers were examined. The optical band gap values of P1 and P2 were found as 1.47 eV and 1.72 eV, respectively. Cyclic voltammetry studies were p...
Citation Formats
S. O. Hacioglu, E. Aktas, G. Hizalan, N. Akbasoglu, A. Çırpan, and L. K. Toppare, “Syntheses of novel fluorinated dibenzo[a,c]phenazine comprising polymers for electrochromic device applications,” NEW JOURNAL OF CHEMISTRY, vol. 46, pp. 14826–14839, 2022, Accessed: 00, 2022. [Online]. Available: