Synthesis of ester-substituted dihydroacridine derivatives and their spectroscopic properties

Autor:	Naoki Yoshioka, Takumi Hosoda, Reiki Tada, Ryota Suzuki, Youhei Miura
Rok vydání:	2016
Předmět:	010405 organic chemistry Chemistry Solvatochromism General Chemistry 010402 general chemistry Photochemistry 01 natural sciences Fluorescence Catalysis 0104 chemical sciences Dipole Intramolecular force Excited state Materials Chemistry Polar effect Moiety Ground state
Zdroj:	New Journal of Chemistry. 40:2920-2926
ISSN:	1369-9261 1144-0546
Popis:	Three dihydroacridine derivatives, 2,7-bis(4-methoxycarbonylphenyl)-9,9-diphenyl-9,10-dihydroacridine (1), 2,8-bis(4-methoxycarbonylphenyl)-10,10-diphenyl-5,10-dihydrophenazasiline (2), and 2,7,9,9-tetraphenyl-9,10-dihydroacridine (3), were prepared and their spectroscopic properties were investigated. These compounds exhibited relatively high quantum yields in a range of solvents. The emission spectra of 1 and 2 displayed large solvatochromic shifts, while the fluorescence solvatochromic behavior was not observed in 3. The intramolecular charge transfer (CT) process from the electron donating moiety at the NH site to the electron withdrawing ester moiety occurs in the excited states of 1 and 2. The increase in the dipole moment induced by the CT process was determined to cause the positive fluorescence solvatochromism. The differences between the excited and ground state dipole moments based on the Lippert–Mataga expression were estimated. The effect of the push–pull substitution in the dihydroacridine π-conjugated system was also discussed using a computational method.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3f39485464d69c45abf0d4c129865de9 https://doi.org/10.1039/c5nj02839f Zobrazit plný text záznamu