Thermally Stable Nitrothiacalixarene Chromophores: Conformational Study and Aggregation Behavior
| Autor: | A. A. Murav’ev, Igor S. Antipin, Marsil K. Kadirov, Sergey A. Katsyuba, Shamil K. Latypov, Tatiana P. Gerasimova, Igor A. Litvinov, Olga Babaeva, Robert R. Fayzullin, Il'dar Kh. Rizvanov, Ayrat R. Khamatgalimov, Svetlana E. Solovieva |
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| Rok vydání: | 2020 |
| Předmět: |
nitrothiacalix[4]arenes
Materials science X-ray diffractometry Absorption spectroscopy 1 2-alternate stereoisomer Mitsunobu alkylation Molecular Conformation 010402 general chemistry Photochemistry 01 natural sciences Article Catalysis lcsh:Chemistry Inorganic Chemistry Phenols reflection-absorption spectroscopy Dynamic light scattering Monolayer TG/DSC analysis Thermal stability Physical and Theoretical Chemistry Thermal analysis Spectroscopy lcsh:QH301-705.5 Molecular Biology Langmuir monolayers 010405 organic chemistry Organic Chemistry Solvatochromism Membranes Artificial General Medicine 0104 chemical sciences Computer Science Applications lcsh:Biology (General) lcsh:QD1-999 DFT study Density functional theory Adsorption |
| Zdroj: | International Journal of Molecular Sciences Volume 21 Issue 18 International Journal of Molecular Sciences, Vol 21, Iss 6916, p 6916 (2020) |
| ISSN: | 1422-0067 |
| Popis: | Achieving high thermal stability and control of supramolecular organization of functional dyes in sensors and nonlinear optics remains a demanding task. This study was aimed at the evaluation of thermal behavior and Langmuir monolayer characteristics of topologically varied nitrothiacalixarene multichromophores and phenol monomers. A nitration/azo coupling alkylation synthetic route towards partially O-substituted nitrothiacalixarenes and 4-nitrophenylazo-thiacalixarenes was proposed and realized. Nuclear magnetic resonance (NMR) spectroscopy and X-ray diffractometry of disubstituted nitrothiacalix[4]arene revealed a rare 1,2-alternate conformation. A synchronous thermal analysis indicated higher decomposition temperatures of nitrothiacalixarene macrocycles as compared with monomers. Through surface pressure/potential-molecular area measurements, nitrothiacalixarenes were shown to form Langmuir monolayers at the air&ndash water interface and, through atomic force microscopy (AFM) technique, Langmuir&ndash Blodgett (LB) films on solid substrates. Reflection-absorption spectroscopy of monolayers and electronic absorption spectroscopy of LB films of nitrothiacalixarenes recorded a red-shifted band (290 nm) with a transition from chloroform, indicative of solvatochromism. Additionally, shoulder band at 360 nm was attributed to aggregation and supported by gas-phase density functional theory (DFT) calculations and dynamic light scattering (DLS) analysis in chloroform&ndash methanol solvent in the case of monoalkylated calixarene 3. Excellent thermal stability and monolayer formation of nitrothiacalixarenes suggest their potential as functional dyes. |
| Databáze: | OpenAIRE |
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