Theoretical Design of Near-Infrared Fluorescent Sensor for F Anion Detection Based on 10-Hydroxybenzo[h]quinoline Backbone

[Image: see text] Proper design and development of near-infrared (NIR) fluorescent sensors is very important for applications in vivo. In this work, we theoretically designed a ratiometric and NIR fluorescent sensor based on the 10-hydroxybenzo[h]quinoline (HBQ) backbone via systematically investigating the substituent effects of electron-donating groups (−NH(2), −CH(3), −C(CH(3))(3)) and electron-withdrawing groups (−NO(2), −CN, −F, −Cl, −CF(3)) at the proton donor site on the proton transfer process in HBQ in both the S(0) and the S(1) states. According to the calculated potential energy profiles along the proton transfer as well as the photophysical properties among all the derivatives, we successfully screened out that 7NH(2)-HBQ is a promising fluorescent sensor exhibiting the near IR emission spectra accompanied by the large Stokes shift. The potential use of 7NH(2)-HBQ for F(–) detection among anions (F(–), Cl(–), and Br(–)) was further studied, and the results showed that 7NH(2)-HBQ is very sensitive and selective toward F(–) based on the intermolecular hydrogen bonding interaction between F(–) and OH bond, forming a new complex FAC(S(0)). The ratiometric change in the fluorescence intensity could be induced by the H–F bond transfer from the O atom to the N atom in the S(1) state.