Synthesis, crystal structures, and two-photon absorption of a series of cyanoacetic acid triphenylamine derivatives

Abstract

A specific series of chromophores (CN1, CN2, CN3, and CN4) have been synthesized, in which contained a triphenylamine moiety as the electron donor (D), a cyanoacetic acid moiety as the electron acceptor (A), vinylene or phenylethyne as the π-bridge, and ethyoxyl groups as auxiliary electron donor (D′) to construct the D-π-A or D′–D-π-A molecular configuration. Photophysical properties of them were systematically investigated. These results show that the chromophores display a solvatochromism (blue shift) and large Stokes shifts for their absorption bands with increasing polarity of the solvent. Furthermore, the chromophore CN4 shows the strongest intensity of two-photon excited fluorescence and largest two-photon absorption cross section (2783 GM) in the near infrared region. Finally, the connections between the structures and properties are systematically investigated relying on the information from linear and nonlinear optical properties, crytsal structures and quantum chemical calculation.