Highly Efficient Multiple-Anchored Fluorescent Probe for the Detection of Aniline Vapor Based on Synergistic Effect: Chemical Reaction and PET

Abstract

A multiple-anchored fluorescent probe ((((hexane-1,6-diylbis(2,7-bis(4-formyl)-phenyl)-9H-fluorine-9,9-diyl))-bis(hexane-6,1-diyl))-bis(9H-carbazole-9,3,6-triyl))-tetrakis(benzene-4,1-diyl))-tetraformyl-(8FP-2F) with eight aldehyde groups was designed and synthesized. The molecule has four branches and highly twisted structure. Furthermore, it tends to self-assemble into nanospheres, which is beneficial for gaseous analyte penetration and high fluorescence quantum efficiency. Among gaseous analytes, detection of aniline vapor is extraordinarily important in the control of environmental issues and human diseases. Herein, 8FP-2F was introduced to detect aniline vapor with distinguished sensitivity and selectivity via simple Schiff base reaction at room temperature. After exposure to saturate aniline vapor, the 89% fluorescence of 8FP-2F was quenched in 50 s and the detection limit was as low as 3 ppb. Further study showed the suitable HOMO/LUMO energy levels and matched orbital symmetry between probe and aniline molecules ensured chemical reaction and PET process work together. The synergistic effect resulted in a significant sensing performance and fluorescence quenching toward aniline vapor. Moreover, the multiple active sites structure of 8FP-2F means it could be applied for constructing many interesting structures and highly efficient organic optoelectronic functional materials.

Multipurpose made colorimetric materials for amines, pH change and metal ion detection

“…Currently, general design of the amine sensors is based on Schiff base motif, where a change in uorescence response can be detected. 43,46,53,54 In contrast, our method is based on the interactions between amine vapours and the conjugated acids [1-H]H+ of the small molecules 1-3 allowing rapid detection using colorimetric approach. Moreover, the reversibility of these interactions can also be achieved offering inexpensive, sensitive, and rapid analytical technology.…”

“…The indicator stripes were prepared by previously reported methodology. 43 Colour measurements were carried out using portable a Datacolor CHECK3 instrument with a standard CIE illuminant D65 (daylight) at 10° observer angle. Prior measurements, the instrument was calibrated against white and black standard plates.…”

“…41 Therefore, several types of sensing materials based on uorescent probes, nanobers, lms of ZnS/PTCDA and TiO 2 /porphyrin with various detection limits and reversibility have been developed. [42][43][44][45][46][47][48][49][50][51] Polydentate hydrazones are conformationally exible ligands, and their structural features display versatile behaviour in metal coordination. For this study, we have chosen compounds 1-3 as they have several structural advantages (Fig.…”

More Interaction Sites and Enhanced Fluorescence for Highly Sensitive Fluorescence Detection of Methamphetamine Vapor via Sidechain Terminal Functionalization of Conjugated Polymers

“…introduced multiple identical recognition units in fluorene dimer to enhance the interaction between the fluorescent molecules and the analytes . Among them, they introduced 8 benzaldehydes in the fluorene dimer, which responded quickly to aniline vapor and the detection limit reached 3 ppb . In addition, they also introduced multiple recognition units to the POSS to increase the interaction sites and achieved rapid fluorescence detection of nitroglycerin (NG) vapor .…”

Aggregation‐Induced Ultraviolet Emission Enhancement and the Electroluminescence Based on New Phenanthrene Derivatives

“…As will be understood, chromophores with larger conjugated structure and strong intramolecular change‐transfer (ICT) usually possess high fluorescence emission . However, these often lead to the spectral bathochromic shift to the visible light region.…”