Synthesis, Optical Properties And Biological Application Of Aniline Derivatives With Two-photon Absorption

Photoelectric functional materials have been widely used in the field of civil, military and other fields,which is one of the focus of many researchers. Nonlinear optical materials, an important photoelectric functional material, has unique optical property and high electrical efficiency. The photophysical and photochemical induced by two-photon absorption possess especial characteristies, which make the two-photon absorption materials have a potential application in a lot of flelds.Based on reviewing literature, the main content were summarized as follows:1. Rational Designed Two-photon Absorption Compounds Based on Benzoxazole Derivatives:Structure-property Relationships and Bio-imaging ApplicationA new series of benzoxazole-based two-photon absorption (2PA) chromophores (T1-6) are synthesized and fully characterized. Among them, T1-4 are linear donor (D)-π-acceptor (A) type fluorophores with various electron-donating groups, while T5 and T6 are multi-branched compounds stemming from T4. Their photophysical properties have been systematically investigated, and then the results of two-photon absorption properties indicate that the highest 2PA cross-section (σ2PA) is 2702 GM for T6 (in DMF). Structure-property relationships of chromophores are further comprehensively discussed based on optical properties, crystal structures and density functional theory (DFT) calculations. In addition, two-photon fluorescence cell imaging experiment demonstrate the potential bio-application of T1-5 with good photostability and low cytotoxicity.2. Four bis-branched A-π-D-π-A triphenylamine-cored derivatives with excellent 2PA properties and appropriate biocompatibility to apply on bio-imagingFour A (acceptor)-π-D (donor)-π-A model triphenylamine-cored compounds (S1-4) with different electron-withdrawing groups have been synthesized and their optical-properties have been systematically investigated. These compounds showed obvious bathochromic shifts of emission peak with increasing solvent polarity. Their two-photon absorption (2PA) cross-section (σ2PA) values were measured by two-photon excited fluorescence (TPEF) method in different solvents, and exhibited large σ2PA values in benzene varied from 2011 to 4173 GM in the near-infrared region. Cytotoxicity tests indicated that all these compounds had good biocompatibility for living cells, both one- and two-photon fluorescence microscopy studies showed the potential application of S1-4 in cell imaging domains due to the large σ2PA and appropriate biocompatibility.