Please use this identifier to cite or link to this item:
https://www.um.edu.mt/library/oar/handle/123456789/70764
Title: | Synthesis and spectroscopic studies of diaza-8-crown-4-dinitrophenyl ethers |
Authors: | Galea, Claudia Makuc, Damjan Szaciłowski, Konrad Plavec, Janez Magri, David C. |
Keywords: | Charge transfer Macrocyclic compounds Fluorescence Spectrum analysis |
Issue Date: | 2020 |
Publisher: | Taylor & Francis |
Citation: | Galea, C., Makuc, D., Szaciłowski, K., Plavec, J., & Magri, D. C. (2020). Synthesis and spectroscopic studies of diaza-8-crown-4-dinitrophenyl ethers. Supramolecular Chemistry, 32(1), 13-22. |
Abstract: | Themacrocycles 3,7-bis(3-nitrophenyl)-1,5,3,7-dioxadiazocane 1 and 3,7-bis(4-nitrophenyl)-1,5,3,7-dioxadiazocane 2 were synthesised by a one-pot reaction with substituted nitroanilines and formaldehyde under acidic conditions. The same reaction with 2-nitroaniline yielded N, N’-(oxybis(methylene))bis (2-nitroaniline) 3 rather than 3,7-bis(2-nitrophenyl)-1,5,3,7-dioxadiazocane 4. The yellow powders 1–3 were characterised by 1H/13C/15N NMR, FTIR and HRMS. The photophysical properties were studied by UV-visible absorption and steady-state fluorescence spectroscopy. Acid dissociation constants were determined by UV-visible absorption titrations in 1:1 (v/v) acetonitrile/water to be 0.80 and 3.1 for the meta- and para-substituted compounds 1 and 2, respectively. Compounds 1 and 2 were discovered to fluoresce in the solid-state, yellow and green, respectively, but not in solution. Density functional theory (DFT) calculations for 1–4 provide insight into the frontier molecular orbital energy levels. These compounds represent a new class of fluorescent heterocyclic building blocks for organic and supramolecular applications. |
URI: | https://www.um.edu.mt/library/oar/handle/123456789/70764 |
Appears in Collections: | Scholarly Works - FacSciChe |
Files in This Item:
File | Description | Size | Format | |
---|---|---|---|---|
Synthesis_and_spectroscopic_studies_of_diaza-8-crown-4-dinitrophenyl_ethers_2020.pdf Restricted Access | 1.5 MB | Adobe PDF | View/Open Request a copy |
Items in OAR@UM are protected by copyright, with all rights reserved, unless otherwise indicated.