Experimental and theoretical insights on the photophysical properties of ester-substituted indolizines

被引:3
|
作者
Vieira, Marcelo M. [1 ]
Dalberto, Bianca T. [1 ]
Padilha, Nathalia B. [1 ]
Junior, Henrique C. S. [1 ]
Rodembusch, Fabiano S. [1 ]
Schneider, Paulo H. [1 ]
机构
[1] Univ Fed Rio Grande Sul UFRGS, Inst Quim, Lab Mol Catalysis LAMOCA, POB 15003, BR-91501970 Porto Alegre, RS, Brazil
关键词
One-pot; Multicomponent reaction; Fluorescence; Indolizines; Selenium; Optical sensor; Ultrasound; NITROGEN-HETEROCYCLES; BIOLOGICAL EVALUATION; DERIVATIVES; FLUORESCENT; EFFICIENT; DESIGN; BENZENE; MODEL;
D O I
10.1016/j.molstruc.2023.136726
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
In this report, we present our latest results on the photophysical properties of substituted indolizines, which were previously obtained through the utilization of ultrasound (US) irradiation, in a one-pot and multicomponent strategy, allowing for a streamlined and straightforward preparation process. The photophysical properties of these derivatives were evaluated in solution using UV-Vis absorption and steady-state fluorescence emission spectroscopy. Our results reveal that these compounds exhibit absorption maxima in the UV-A-violet region. The electronic transitions could be related to spin and symmetry allowed 1 pi ->pi* electronic transitions. The indolizines present fluorescence in the violet-to-green region. Both ground and excited states were shown to be tailored by the substituents in the indolizine core. In addition, the role of the solvent in the deactivation of the excited state proved to be critical in the successful exploration of these compounds as optical sensors for benzene. When benzene was added to the ethanolic solution, the indolizines usually exhibited fluorescence quenching, with a linear relationship between the amount of benzene and the emission intensity. Theoretical calculations were also employed to gain a deeper understanding of the solute-solvent interactions.
引用
收藏
页数:10
相关论文
共 50 条
  • [1] Experimental and theoretical studies of photophysical properties of N-Substituted iminocoumarins
    Jlaiel, Rihab
    Elleuch, Slim
    Abid, Souhir
    Abid, Younes
    Ammar, Houcine
    OPTICAL MATERIALS, 2022, 134
  • [2] Synthesis, photophysical, and electrochemical properties of 2,5-diaryl-indolizines
    Amaral, Monica F. Z. J.
    Deliberto, Laila A.
    de Souza, Camila R.
    Naal, Rose M. Z. G.
    Naal, Zeki
    Clososki, Giuliano C.
    TETRAHEDRON, 2014, 70 (20) : 3249 - 3258
  • [3] Synthesis and photophysical properties of 2-aryl-5-carbonyl indolizines
    Bertallo, Camila R. S.
    Berlim, Leonardo S.
    Olivier, Danilo S.
    Arroio, Thais R.
    Ito, Amando S.
    Clososki, Giuliano C.
    DYES AND PIGMENTS, 2022, 198
  • [4] Bichalcophenes: A Concise Synthesis of Formyl Ester- and Cyano Ester-Substituted Bithiophenes, Bifurans, and Furanothiophenes
    Farahat, Abdelbasset A.
    Kumar, Arvind
    Barghash, Alaa El-Din M.
    Goda, Fatma E.
    Eisa, Hassan M.
    Boykin, David W.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (01) : 167 - 170
  • [5] An experimental and theoretical study on the photophysical properties of methylene green
    Glusko, Carlos A.
    Previtali, Carlos M.
    Vera, D. Mariano A.
    Chesta, Carlos A.
    Montejano, Hernan A.
    DYES AND PIGMENTS, 2011, 90 (01) : 28 - 35
  • [6] Synthesis and electroluminescent properties of red emissive iridium(III) complexes with ester-substituted phenylquinoline ligands
    Tong, Bihai
    Mei, Qunbo
    Chen, Dongyang
    Lu, Mangeng
    SYNTHETIC METALS, 2012, 162 (17-18) : 1701 - 1706
  • [7] Fluorescence and photophysical properties of xylene isomers in water: with experimental and theoretical approaches
    Khan, Muhammad Farooq Saleem
    Wu, Jing
    Liu, Bo
    Cheng, Cheng
    Akbar, Mona
    Chai, Yidi
    Memon, Aisha
    ROYAL SOCIETY OPEN SCIENCE, 2018, 5 (02):
  • [8] Combined Experimental and Theoretical Investigation into the Photophysical Properties of Halogenated Coelenteramide Analogs
    Afonso, Ana Carolina P.
    Gonzalez-Berdullas, Patricia
    Esteves da Silva, Joaquim C. G.
    da Silva, Luis Pinto
    MOLECULES, 2022, 27 (24):
  • [9] Influence of (de)protonation on the photophysical properties of phenol-substituted diazine chromophores: experimental and theoretical studies
    Hodee, Maxime
    Lenne, Augustin
    Rodriguez-Lopez, Julian
    Robin-le Guen, Francoise
    Katan, Claudine
    Achelle, Sylvain
    Fihey, Arnaud
    NEW JOURNAL OF CHEMISTRY, 2021, 45 (40) : 19132 - 19144
  • [10] Theoretical Study of the Mechanism of Palladium(0)-Catalyzed Intramolecular [2+2+2] Cycloaddition of Ester-Substituted Alkynes
    Yamamoto, Yoshihiko
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (48) : 7455 - 7465