New 9-Aminoacridine Derivative: Synthesis, Study and Potential Application as pH Indicator in Organic Solvents

Stroppa, Pedro H. F.; Glanzmann, Nícolas; Duarte, Lucas M.; Sato, Renata T.; Oliveira, Marcone A. L. de; Silva, Adilson D. da

doi:10.21577/0103-5053.20170084

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Articles • J. Braz. Chem. Soc. 28 (12) • Dec 2017 • https://doi.org/10.21577/0103-5053.20170084 linkcopy

New 9-Aminoacridine Derivative: Synthesis, Study and Potential Application as pH Indicator in Organic Solvents

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Abstract

In this work, we describe the synthesis of a novel 9-aminoacridine derivative that presents surprisingly different colors when exposed to neutral, acidic or basic mediums with potential application as pH indicator in organic solvents. Furthermore, pKa and molar absorptivity values were determined and theoretical studies supported by density functional theory (DFT) calculations were performed to elucidate the different structures of this compound.

Keywords:
9-aminoacridine derivative; pH indicator; organic medium

	Solvent	Wavelength / nm	Absorptivity / (L mol^-1 cm^-1)	R-squared
Protonated TNA	ethanol	368	16495.9 ± 199.8	0.998
	methanol	363	15853.9 ± 169.6	0.998
Neutral TNA	ethanol	416	12300.3 ± 74.4	0.999
	methanol	410	13263.3 ± 90.3	0.999
Deprotonated TNA	ethanol	468	16151.6 ± 104.9	0.999
	methanol	482	16791.3 ± 85.3	0.999
9-AAa	-	-	16300	-

	MO_t	λ_Exp / λ_max / nm	λ_Calc / nm	OS	ΔE / eV
Protonated TNA	HOMO → LUMO	400-450 / 400	405	0.1205a	3.06
Neutral TNA	HOMO → LUMO	400-510 / 416	461	0.0495	2.69
	HOMO → LUMO + 1		437	0.4672a	2.83
Deprotonated TNA	HOMO → LUMO	400-565 / 500	527	0.5988a	2.35
	HOMO → LUMO + 1		514	0.0666	2.41
	HOMO → LUMO + 3		480	0.0522	2.58
	HOMO → LUMO + 2		441	0.0116	2.81

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[TFN1] ^a
9-AA: value obtained from the literature.²⁷