Synthesis of High-Fluorescent Diphenyl-anthracene Derivatives and Application in Detection of Nitroaromatic Explosives and Fingerprint Identification.

Abstract

The development of high-intensity fluorescent materials is always the focuses and forefront projects because of their important applications in displays, sensing and detection fields. In recent years, the detection of explosives has attracted increasing attention due to security and counterterrorism issues. Herein, two diphenyl-anthracene (DPA) derivatives were designed and synthesized by introducing strong electron withdrawing fluorine atoms and cyano-groups to DPA, which exhibited strong fluorescence both in the solution and solid phase with the absolute quantum yields up to 70.4 % and 45.9 % respectively. The detection behavior of nitroaromatic explosives such as picric acid (PA), 2,4,6-trinitrotoluene (TNT) and 3-Nitropropionic acid (3-NP) also shows good sensitivity with the quenching constant as high as 6.3×104 L mol-1 . Theoretical calculation demonstrates that the fluorescence quenching behavior of the two DPA derivatives is caused by the behavior of photoinduced electron transfer (PET) and the resonance energy transfer (RET) studies explained the higher sensitivity and selectivity of both compounds towards PA than other nitro-containing explosives. Furthermore, the strong solid-state fluorescence of the DPA derivatives also shows excellent advantages in enhancing latent fingerprint recognition.