Synthesis, structure and spectral properties of 9-diarylamino-substituted acridines

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• 作者：Viacheslav A. Sazhnikov ; Artem A. Khlebunov ; Sergey K. Sazonov ; Artem I. Vedernikov ; Andrei A. Safonov ; Alex ; er A. Bagatur鈥檡ants ; Lyudmila G. Kuz鈥檓ina ; Judith A.K. Howard ; Sergey P. Gromov ; Michael V. Alfimov
• 关键词：Acridine derivatives ; X-ray structures ; Fluorescence ; Solvatofluorochromism ; DFT calculations
• 刊名：Journal of Molecular Structure
• 出版年：5 December, 2013
• 年：2013
• 卷：1053
• 期：Complete
• 页码：79-88
• 全文大小：1090 K

文摘

The synthesis of three 9-diarylamino-substituted acridines is reported. The compounds of the donor-acceptor type - N,N-diphenylacridin-9-amine (ong class="boldFont">1ong>), 2,7-dimethyl-N,N-bis(4-methylphenyl)acridin-9-amine (ong class="boldFont">2ong>), and 2,7-bis(1-methyl-1-phenylethyl)-N,N-bis[4-(1-methyl-1-phenylethyl)phenyl]acridin-9-amine (ong class="boldFont">3ong>) were characterized by IR, ¹H and ¹³C NMR, mass-spectral and elemental analysis. The crystal structures of compounds ong class="boldFont">1ong>-ong class="boldFont">3ong> and their protonated forms were determined by X-ray diffraction analysis. The absorption and fluorescence spectra were measured in various solvents. Solvatochromic shifts and dependence of the fluorescence quantum yields on the solvent polarity and protonation suggest the use of these compounds as chemical sensors. An example of a sensor material based on compound ong class="boldFont">2ong> is presented. Density functional theory calculations of the structures and time-dependent density functional theory calculations of the gas-phase excitation and emission energies of ong class="boldFont">1ong> were performed at the PBE0/SVP level of theory.