Insight into fluorescence properties of 14 selected toxic single-ring aromatic compounds in water: Experimental and DFT study

doi:10.1007/s11783-020-1219-z

Front. Environ. Sci. Eng.

2020, Vol. 14

Issue (3) : 42 https://doi.org/10.1007/s11783-020-1219-z

RESEARCH ARTICLE

Insight into fluorescence properties of 14 selected toxic single-ring aromatic compounds in water: Experimental and DFT study

Muhammad Farooq Saleem Khan^1,^2,³, Jing Wu^1,²(

), Cheng Cheng¹, Mona Akbar¹, Chuanyang Liu^1,², Bo Liu¹, Jian Shen¹, Yu Xin³

¹. State Key Joint Laboratory of Environment Simulation and Pollution Control, School of Environment, Tsinghua University, Beijing 100084, China
². Research Institute for Environmental Innovation (Suzhou), Tsinghua University, Suzhou 215000, China
³. School of Physical Science and Technology & Jiangsu Key Laboratory of Thin Films, Soochow University, Suzhou 215006, China

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Abstract

• The fluorescence peak location of 14 compounds interpreted at protein-like region.

• The p-electron system inside aromatic ring contributes to the fluorophore region.

• Functional group variation effects the emission spectra.

• Decrease in quantum yield and increase in DE is due to atomic weight F>Cl>Br>I.

• Theoretically results are in line with experimental ones.

Various single-ring aromatic compounds in water sources are of great concern due to its hazardous impact on the environment and human health. The fluorescence excitation-emission matrix (EEMs) spectrophotometry is a useful method to identify organic pollutants in water. This study provides a detailed insight into the fluorescence properties of the 14 selected toxic single-ring aromatic compounds by experimental and theoretical analysis. The theoretical analysis were done with Time-Dependent Density Functional Theory (TD-DFT) and B3LYP/6-31G (d,p) basis set, whereas, Polarizable Continuum Model (PCM) was used to consider water as solvent. The selected compounds displayed their own specific excitation-emission (Ex/Em) wavelengths region, at Ex<280 nm and Em<340 nm, respectively. Whereas the theoretical Ex/Em was observed as, Ex at 240 nm–260 nm and Em at 255 nm–300 nm. Aniline as a strong aromatic base has longer Em (340 nm) than alkyl, carbonyl, and halogens substituted benzenes. The lone pair of electrons at amide substituent serves as a p-electron contributor into the aromatic ring, hence increasing the stability and transition energy, which results in longer emission and low quantum yield for the aniline. The fluorescence of halogenated benzenes illustrates an increase in the HOMO-LUMO energy gap and a decrease in quantum yield associated with atomic size (F>Cl>Br>I). In this study the theoretical results are in line with experimental ones. The understanding of fluorescence and photophysical properties are of great importance in the identification of these compounds in the water.

Keywords Fluorescence Photophysical properties Effect of the substituent Toxic aromatic compounds

Corresponding Author(s): Jing Wu

Just Accepted Date: 13 February 2020 Issue Date: 11 March 2020

Cite this article:

Muhammad Farooq Saleem Khan,Jing Wu,Cheng Cheng, et al. Insight into fluorescence properties of 14 selected toxic single-ring aromatic compounds in water: Experimental and DFT study[J]. Front. Environ. Sci. Eng., 2020, 14(3): 42.

URL:

https://academic.hep.com.cn/fese/EN/10.1007/s11783-020-1219-z
https://academic.hep.com.cn/fese/EN/Y2020/V14/I3/42

Tab.1 Aromatic compounds with a single benzene ring

Fig.1 Experimental EEMs of (a) Benzene, (b) Toluene, (c) Ethylbenzene, (d) Isopropylbenzene, (e) Anisole, (f) Aniline, (g) Benzaldehyde, (h) Benzonitrile, (i) 2-phenylethanol, (j) Methylbenzoate, (k) Fluorobenzene, (l) Chlorobenzene, (m) Bromobenzene, (n) Iodobenzene.

Fig.2 Experimental Ex/Em of single benzene ring aromatic compounds in water.

Tab.2 Ex/Em of fluorescence peak of single benzene ring aromatic organic compounds

Tab.3 Fluorescence and electronic details of benzene, toluene, ethylbenzene, and isopropyl benzene

Tab.4 Fluorescence and electronic details of nitrogen and oxygen, containing substituents on the benzene ring

Tab.5 Fluorescence and electronic details of halogen substituents on the benzene

Fig.3 Excitation and Emission wavelength (nm) of 14 selected single-ring aromatic compounds in water.

Fig.4 HOMO and LUMO energy gap (DEgap) and quantum yield of halogenated benzene in water.

Fig.5 HOMO and LUMO energy gap (DEgap) and quantum yield of 14 selected single-ring aromatic compounds in water

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