Synthesis, spectroscopic and photophysical studies of xanthene derivatives

被引:21
作者
Taghartapeh, Mohammad Ramezani [1 ]
Pesyan, Nader Noroozi [1 ]
Rashidnejad, Hamid [1 ]
Khavasi, Hamid Reza [2 ]
Soltani, Alireza [3 ]
机构
[1] Urmia Univ, Fac Chem, Dept Organ Chem, Orumiyeh 57159, Iran
[2] Shahid Beheshti Univ, Fac Sci, Dept Chem, Tehran, Iran
[3] Golestan Univ Med Sci, Joints Bones & Connect Tissue Res Ctr, Gorgan, Iran
关键词
Xanthene; Hirshfeld surface analysis; Spectroscopic analysis; DFT and TD-DFT calculations; Non-liner optical parameters; ONE-POT SYNTHESIS; X-RAY; VIBRATIONAL-SPECTRA; MOLECULAR-STRUCTURE; ANTIOXIDANT ACTIVITY; DFT; ACID; 2'; 6'-DIMETHOXYFLAVONE; DIBENZOXANTHENES; CYTOTOXICITY;
D O I
10.1016/j.molstruc.2017.08.054
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
We report on the experimental, crystal structure and computational investigation of a new class of xanthenes obtained by the reaction of salicylaldehyde and its derivatives with, 5,5-Dimethylcyclohexane-1,3-dione (Dimedone). The synthesized xanthenes were characterized by stateof-the-art techniques, such as IR, Raman, H-1 and C-13 NMR, Single Crystal X-ray crystallography, UV Vis and photophysical measurements. The structure, ground- and excited-state properties of one xanthene derivative was investigated using Density Functional Theory (DFT) and Time-Dependent DFT (TD-DFT) calculations with and without solvent (ethanol). The optimized geometries and predicted IR frequencies were in good agreement with experimental data. Hirshfeld surface analyses were carried out to gain insight on the close-contact interactions of the crystal, where hydrogen showed the highest contribution (66.1%). The synthetic route proposed in this work does not use any catalysts and leads to high yields (75-85%), therefore being an interesting alternative to synthesize xanthene derivatives. (C) 2017 Elsevier B.V. All rights reserved.
引用
收藏
页码:862 / 873
页数:12
相关论文
共 59 条
[1]   Crystallography and computational electronic structure investigations on 14-(3, 4, 5-trimethoxyphenyl)-14H-dibenzo[a,j]xanthene [J].
Anandhan, Karnambaram ;
Boobalan, Maria Susai ;
Venkatesan, Perumal ;
Ilangovan, Andivelu ;
Kaushik, Mahabir Prasad ;
Arunagiri, Chidambaram .
JOURNAL OF MOLECULAR STRUCTURE, 2015, 1097 :185-198
[2]  
[Anonymous], J RES NATL BUR STA A
[3]  
[Anonymous], XAREA VERS 1 31
[4]  
[Anonymous], PHYS CHEM
[5]  
[Anonymous], PROG INORG CHEM
[6]  
[Anonymous], CHEM SOC
[7]  
[Anonymous], 1978, ADV QUANTUM CHEM
[8]  
[Anonymous], RES J CHEM SCI
[9]   Structural, vibrational and DFT studies of di-(pipecolinium acid) squarate [J].
Bartoszak-Adamska, Elzbieta ;
Dega-Szafran, Zofia ;
Komasa, Anna ;
Szafran, Miroslaw .
VIBRATIONAL SPECTROSCOPY, 2017, 88 :106-116
[10]   pKa determinations of xanthene derivates in aqueous solutions by multivariate analysis applied to UV-Vis spectrophotometric data [J].
Batistela, Vagner Roberto ;
Pellosi, Diogo Silva ;
de Souza, Franciane Dutra ;
da Costa, Willian Ferreira ;
de Oliveira Santin, Silvana Maria ;
de Souza, Vagner Roberto ;
Caetano, Wilker ;
Moises de Oliveira, Hueder Paulo ;
Scarminio, Ieda Spacino ;
Hioka, Noboru .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2011, 79 (05) :889-897