Fluorescent detection of amidinium-carboxylate and amidinium formation using a 1,8-diphenylnaphthalene-based diamidine: dicarboxylic acid recognition with high fluorescence efficiency

Enlightening the Path to Protein Engineering: Chemoselective Turn-On Probes for High-Throughput Screening of Enzymatic Activity

“…403,420−422 These interactions can induce fluorescence by electronic changes of the probe: Nonbonding electron pairs of amines or adjacent electrondonating groups are known to quench fluorescence by PET processes, which can be restored by coordination of the amines to carboxylic acids. 408,422 Similarly, quenching has been observed by binding of amine probes to Cu 2+ ions. By coordination and thus scavenging of the Cu 2+ ions by carboxylates, the probe's fluorescence emission can be effectively restored.…”

“…A challenge in sensing carboxylic acid is the selective detection and the differentiation of acids. ,, One method to improve selectivity is introducing multiple recognition sites at the probe. , Many of the assays require nonaqueous conditions or apolar/aprotic solvents ( e.g ., chloroform) to prevent competitive interactions between the solvent and the binding sites of the probe. − …”

1,8‐Diarylnaphthalenes: Synthesis, Properties, and Applications

“…4,4’‐(Naphthalene‐1,8‐diyl)dibenzonitrile 73 , prepared using the Suzuki methodology, served as the starting material in the synthesis of diamidine 74 (Scheme 21). [11] The latter turned out to be an effective fluorescent probe for dicarboxylic acids: upon interaction of diamidine 74 with dicarboxylic acids having a sufficient for binding to diamidine distance between two carboxyl groups, a 1 : 1 complex was formed, with a fluorescence band at 410–430 nm corresponding to amidinium carboxylate. Upon complexation with monocarboxylic and dicarboxylic acids having an insufficient distance between two carboxyl groups, the maximum emission was observed at 440–470 nm.…”

“…1,8-Diarylnaphthalenes 1 have attracted considerable attention of organic, physic organic and material chemists for decades due to unusual geometry and, consequently, properties (for selected articles, see Refs. [1][2][3][4][5][6][7][8][9][10][11][12][13][14]). It is well known that, in the absence of any steric restrictions, two aryl rings prefer the Tarrangement based on the electrostatic interaction between the π-system of one ring and the polarized CÀ H bond of the other one.…”

“…[28] The advantages of the hindered or impossible rotation of peri-aryl rings have already been exploited in a variety of attractive practical applications. 1,8-Diarylnaphthalenes have been studied as photoluminescent sensors and stereodynamic switches, [7,8] blue-transparent frequency doublers, [10] fluorescent sensors for various types of organic and inorganic compounds, [11][12][13] materials for creating high-performance blue and green organic light-emitting diodes. [9] And this is not a complete list.…”