850568-12-6Relevant articles and documents
Carboxylic acid recognition of an N-ethyl-substituted diamidine having a diphenylnaphthalene unit in competing protic solvents
Hoshihara, Yuki,Kusukawa, Takahiro,Matoba, Keisuke,Nakajima, Akane,Tanaka, Syugo
, (2021/08/13)
A new diphenylnaphthalene-based diamidine (1) having an N-ethyl-substituent to improve its solubility has been designed and synthesized for the recognition of dicarboxylic acids. The diamidine 1 forms 1:1 complexes with the α,ω-dicarboxylic acids in the competing protic solvent, MeOH, using the charge-assisted hydrogen bonding (i.e., formation of amidinium-carboxylate), and the formation of the complexes was determined by 1H NMR and DOSY NMR spectroscopies in a high concentration (2.0 mM). However, at a low concentration (25 μM), the turn-on fluorescence detection of the dicarboxylic acids was not successful because the diamidine 1 emits in MeOH before recognizing the carboxylic acids. Interestingly, the diamidine 1 does not emit in 2-propanaol before recognizing the α,ω-dicarboxylic acids, and succeeded in the detection of a dicarboxylic acid (turn-on response) in the protic solvent, 2-propanol. The interesting tight binding of the diamidine 1 with α,ω-dicarboxylic acids was observed in 2-propanol-d8 using 1H NMR and the restriction of the rotation of the phenyl rings of the 1,8- diphenylnaphthalene unit was also observed. These fluorescence and binding characteristics of the N-ethyl-substituted diamidine 1 are applicable for the detection of carboxylic acids in a protic solvent.