Journal
MOLECULES
Volume 27, Issue 19, Pages -Publisher
MDPI
DOI: 10.3390/molecules27196248
Keywords
fluorescein diglycolic acid; calcium; multivariate; DFT; principal component analysis
Funding
- Universiti Malaya (UM) International Collaboration Grant [ST005-2022]
- UM KW IPPP-Research Maintenance Fee (RMF) [RMF1433-2021]
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Computational and experimental approaches were used to design a fluorescein derivative as a calcium ion (Ca2+) receptor. The study showed that the fluorescein derivative exhibited good selectivity and discrimination towards Ca2+ over potassium ion (K+) and magnesium ion (Mg2+). The results suggest that this method could be applied to the determination of cationic plant macronutrients in precision agriculture and other applications.
Computational and experimental approaches were adopted to utilize a chromophore diglycolic functionalized fluorescein derivative as a Ca2+ receptor. Fluorescein diglycolic acid (Fl-DGA, 1) was synthesized and used in multivariate determination of Ca2+ and K+. Full-structure computation shows that the complexes of 1 and Ca2+ have comparable energies regardless of additional interaction with lactone moiety. The initial formation of diglycolic-Ca2+ complex followed by macrocyclization is thermodynamically disfavored. A U-shaped pre-organized 1 allows Ca2+ to interact simultaneously with diglycolic and lactone motifs. Both motifs actively participate in Ca2+ recognition and the eleven methylene units in the undecyl arm provides excellent flexibility for reorganization and optimum interaction. Principal component analysis (PCA) of computational molecular properties reveals a simple method in evaluating motifs for cation recognition. Fragment models support full-structure results that negative charge causes significant structural changes, but do not reproduce the full extent of C-O bond breaking observed in the latter. Experimental optical responses show that 1 is selective towards Ca2+ and discriminates against K+ and Mg2+. PCA of emission intensities affords distinct clusters of 0.01, 0.1 and 1 mM Ca2+ and K+, and suggests applicability of this technique for simultaneous determination of cationic plant macronutrients in precision agriculture and a wide variety of other applications.
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