199339-77-0Relevant academic research and scientific papers
Fluorescent detection of amidinium-carboxylate and amidinium formation using a 1,8-diphenylnaphthalene-based diamidine: Dicarboxylic acid recognition with high fluorescence efficiency
Kusukawa, Takahiro,Tanaka, Syugo,Inoue, Kouta
, p. 4049 - 4056 (2014/06/09)
A 1,8-diphenylnaphthalene-based diamidine (1) 'turn-on' fluorescent probe for the detection of dicarboxylic acids has been designed and synthesized. The fluorescence spectra of the diamidine 1 with carboxylic acids that showed two different fluorescence bands, which corresponded to the amidinium-carboxylate (λem=410-430 nm) and amidinium (λem=440-470 nm as a broad band, which consisted from two peaks) formation, were confirmed by DOSY NMR and TD-DFT calculations. The complexation of diamidine 1 with dicarboxylic acids, which have sufficient distances between the two carboxylic groups for binding to the diamidine 1 (dicarboxylic acids 3, 4, and α,ω-dicarboxylic acids 6 (C6-C20)), showed the formation of 1:1 complexes (i.e., amidinium-carboxylate formation). On the other hand, for the complexation with monocarboxylic acids and dicarboxylic acids having insufficient distances between the two carboxylic groups (benzoic acid 5, acetic acid 7, and α,ω-dicarboxylic acids 6 (C 3-C5)), formation of the amidinium (1·2H +) was observed. Relatively similar binding constants (10 -5) for the complexation of the diamidine 1 with dicarboxylic acids 6, which depend on their chain length (strain), were observed due to the flexibility of the 1,8-diphenylnaphthalene unit. Additionally, for the complexation of the diamidine 1 with dicarboxylic acids, higher fluorescence quantum yields (Φfl: up to 80%) were observed when compared to the binding of the diamidine 2 (Φfl: up to 35%).
Exploring the selectivity of the Suzuki-Miyaura cross-coupling reaction in the synthesis of arylnaphthalenes
Lima, Carlos F.R.A.C.,Rodriguez-Borges, José E.,Santos, Luís M.N.B.F.
experimental part, p. 689 - 697 (2011/03/19)
A series of 1-arylnaphthalenes and 1,8-diarylnaphthalenes were synthesized by the Suzuki-Miyaura cross-coupling methodology showing significant differentiation in the yields and selectivity between aryl rings with electron donating (higher yields), and el
