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    Probing the supramolecular features via pi-pi interaction of a di-iminopyrene-di-benzo-18-crown-6-ether compound: experimental and theoretical study

    Year: 2020

    Journal: RSC Adv., Volume 10, OCT 21, page 38304–38315

    Authors: Coroaba, Adina; Isac, Dragos-Lucian; Al-Matarneh, Cristina; Vasiliu, Tudor; Ibanescu, Sorin-Alexandru; Zonda, Radu; Ardeleanu, Rodinel; Neamtu, Andrei; Timpu, Daniel; Nicolescu, Alina; Mocci, Francesca; Maier, Stelian S.; Laaksonen, Aatto; Abadie, Marc Jean Medard; Pinteala, Mariana

    A novel DPyDB-CN-18C6 compound was synthesised by linking a pyrene moiety to each phenyl group of dibenzo-18-crown-6-ether, the crown ether, through -HCN- bonds and characterized by FTIR, H-1-NMR, C-13-NMR, TGA, and DSC techniques. The quantitative C-13-NMR analysis revealed the presence of two position isomers. The electronic structure of the DPyDB-CN-18C6 molecule was characterized by UV-vis and fluorescence spectroscopies in four solvents with different polarities to observe particular behavior of isomers, as well as to demonstrate a possible non-bonding chemical association (such as ground- and excited-state associations, namely, to probe if there were forming dimers/excimers). The interpretation of the electronic structure was realized through QM calculations. The TD-CAM-B3LYP functional, at the 6-311+G(d,p) basis set, indicated the presence of predominant pi -> pi* and mixed pi -> pi* + n -> pi* transitions, in line with the UV-vis experimental data. Even though DPyDB-CN-18C6 computational studies revealed a pi-extended conjugation effect with predominantly pi -> pi* transitions, thorough fluorescence analysis was observed a weak emission, as an effect of PET and ACQ. In particular, the WAXD analysis of powder and thin films obtained from n-hexane, 1,2-dichloroethane, and ethanol indicated an amorphous organization, whereas from toluene a smectic ordering was obtained. These results were correlated with MD simulation, and it was observed that the molecular geometry of DPyDB-CN-18C6 molecule played a defining role in the pyrene stacking arrangement.
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