A Facilely Synthesized Dual‐State Emission Platform for Picric Acid Detection and Latent Fingerprint Visualization

Abstract

To achieve a highly efficient, dual‐state emission platform for picric acid (PA) detection and latent fingerprint (LFP) visualization, flexible alkyl chains have been facilely attached to the commercial organic dye 3,4,9,10‐perylenetetracarboxylic dianhydride to provide the target perylenetetracarboxylate molecules PTCA‐C4, PTCA‐C6, and PTCA‐C12. Interestingly, all these molecules exhibited impressive fluorescence characteristics with high photoluminescence quantum yields (PLQYs) of around 93.0 % in dilute solution. Also, emissive features were observed in the solid state because close molecular packing is prevented by the alkyl chains, especially for PTCA‐C6, which has a high PLQY value of 49.0 %. Benefiting from its impressive fluorescence performance in both solution and as aggregates, PTCA‐C6 was used as a dual‐state emission platform for PA detection and also LFP visualization. For example, double‐responsive fluorescence quenching in solution was observed in PA detection studies, resulting in high quenching constants (KSV) and also low limit‐of‐detection values. Furthermore, the fingerprint powder based on PTCA‐C6 also presented an impressive performance on various substrates in terms of fluorescence intensity and resolution, clearly providing the specific fine details of latent fingerprints. These results demonstrate that the facilely synthesized PTCA‐C6 with efficient dual‐state emission exhibits great potential in the real‐world applications of PA detection and LFP visualization.

Rational Design and Facile Synthesis of Dual‐State Emission Fluorophores: Expanding Functionality for the Sensitive Detection of Nitroaromatic Compounds

“…Further, the limit of detection (LOD) and quenching constant (K SV ) for PA sensing can be calculated to be 2.10×10 −7 M and 7.43×10 3 M −1 , respectively. These data are comparable to what has been observed for the reported fluorescent probes [65,72,73] . The low LOD and larger K SV value mean the excellent sensitivity of the probe 4 a for PA detection in solution.…”

“…Today, there are many methods for NACs detection, such as fluorescence sensing, [64] mass spectrometry, [66] surface‐enhanced Raman spectrometry [67] and capillary electrophoresis, [68] etc. Among them, fluorescence detection is more attractive owing to its good selectivity, high sensitivity, operational simplicity and on‐site detection [62–65] . It is worth noting that, although there are many kinds of NACs fluorescent sensing materials reported before, such as porous organic polymers, [62] metal‐organic frameworks [69] and metal complexes, [70] etc., most of probes suffer from the different disadvantages, for example, the single detection mode.…”

“…It is known that, there are mainly two other mechanisms contributing to the high sensitivity of fluorescence probes in NACs detection, fluorescence resonance energy transfer (FRET) and photoinduced electron transfer (PET) [65] . Therefore, to further investigate the mechanism, the absorption spectra of PA, DNP, NP, NA, NBA and NBAc, and the fluorescence spectra of 4 a in solution were recorded.…”

“…It is known that, there are mainly two other mechanisms contributing to the high sensitivity of fluorescence probes in NACs detection, fluorescence resonance energy transfer (FRET) and photoinduced electron transfer (PET). [65] Therefore, to further investigate the mechanism, the absorption spectra of PA, DNP, NP, NA, NBA and NBAc, and the fluorescence spectra of 4 a in solution were recorded. As shown in Figure 7, the optical overlap of the absorption of PA, DNP and NA and the emission of 4 a can be obviously observed, thus indicating that FRET may be the reason for the high sensitivity in PA, DNP and NA.…”

Dual-State Emission (DSE) in Organic Fluorophores: Design and Applications

“…Meng and collaborators have recently published an example (52). 184 This compound was used in solution to detect the explosive picric acid and was also employed in the solid state to collect fingerprints (FPs) in crime scenes (Figure 24).…”