Open AccessSodium ion chemosensor of 3-oxo-3H-benzo[f]chromen-2-carboxylic acid: An experimental and computational study
Author(s) -
Jamaludin Al Anshori,
Andi Rahim,
Ajar Faflul Abror,
Ace Tatang Hidayat,
Tri Mayanti,
Muhammad Yusuf,
Juliandri Juliandri,
Ace Tatang Hidayat
Publication year - 2021
Publication title -
journal of the serbian chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.227
H-Index - 45
eISSN - 1820-7421
pISSN - 0352-5139
DOI - 10.2298/jsc200929022a
Subject(s) - chemistry , knoevenagel condensation , fluorescence , density functional theory , chelation , metal ions in aqueous solution , stoichiometry , photoinduced electron transfer , carboxylic acid , photochemistry , metal , ion , yield (engineering) , electron transfer , inorganic chemistry , computational chemistry , organic chemistry , materials science , physics , quantum mechanics , metallurgy , catalysis
A fluorescence compound with the typical skeleton of benzocoumarin was synthesized and its interaction with various metal ions was evaluated. The synthesis was performed via Knoevenagel condensation whereas identification of the product was accomplished by various spectroscopic techniques. The chemosensor test against representative metal ions was monitored by fluorescence spectrophotometry. A density functional theory calculation (DFT, functional/basis set; M06/6-31G (d, p)) was also performed to clarify the experimental results and to confirm the mechanism of interaction. 3-Oxo-3H-benzo- [f]chromene-2-carboxylic acid 1 was obtained as a yellow solid in 60 % chemical yield. Melting point; 235.6?236.7?C and ?max UV/Vis, ?em and Stokes shift (MeOH, nm) of 374, 445 and 71 nm, respectively. The structure of the compound was identified based on spectroscopic data and literature comparison. Compound 1 exhibited a chelation quenched fluorescence (CHQF) phenomenon selectively toward the Na+, with a binding stoichiometry (1:2) and LoD and LoQ of 0.14 and 0.48 mg/L, respectively. Based on DFT calculations, compound 1 chelated Na+ through mechanism of oxidative (1:1 equivalent) and reductive (2:1 equivalent) photoinduced electron transfer (PET), correspondingly