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Synthesis and third-order nonlinear properties of D-A-D structure acridone derivatives

Jianhong Jia, Ziqiang Zhu, Chengtao Gong, Mingyan Li, Jiuming Zhang, Yinglin Song, and Yuanbin She

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, People’s Republic of China

 

E-mail: zgdjjh@163.com

Received: 26 March 2022  Accepted: 29 November 2022

Abstract:

Six acridone derivatives with 2,7-bis-substituted D-A-D structures were designed and synthesized. Z-scan technology and DFT theoretical calculations studied the influence of the structure on the nonlinear optical properties. The ultraviolet–visible spectrum of compound YB3 with bis-(diphenylamino)phenyl substitution shows an ultraviolet maximum absorbance at 364 nm. This wavelength is red-shifted by 44 nm compared to compound YB1 with bis-(methoxyphenyl) substitution (at 320 nm). This change is interpreted as a strengthened electron supply and expanded conjugate system by the electron-donating bis-(diphenylamino)phenyl substitution groups. Cyclic voltammetry and DFT calculations show that the dihedral angle between electron-donating group and electron-withdrawing group (The dihedral angle is defined by two atoms on each side of the bond between the donor and the acceptor for a total of four connected carbon atoms.) should be as small as possible. Structure (2,7-bis-(4-(diphenylamino)phenyl)-10-dodecylacridin-9(10H)-one (YB3) shows the optimal third-order NLO behavior with a second-order NLO hyperpolarizability γ of 8.665 × 10–33 esu, which is 1.6 times higher than that of YB1 (γ = 5.136 × 10–33 esu), and 1.7 times that of YA4 with bis-(4-(-di-(4-methoxyphenyl)amino)phenyl) 2,7-substitution of the 10-dodecylacridin-9(10H)-one.

Graphical abstract

Keywords: Acridone derivatives; NLO; Electronic donor; Z-scan; DFT

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-022-02612-3

 

Chemical Papers 77 (4) 2089–2101 (2023)

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