Isatin hydrazones based on phenanthroline like skeleton – synthesis

Isatin hydrazones based on phenanthroline like skeleton – synthesis

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PoužívateľVedecká prácaDizajnDiskusná interakcia
RNDr. Žofia Nižnanská PhD.100%100%-
Mgr. Jana Jakubčinová PhD.100%100%100%
Mgr. Róbert Šandrik100%100%100%
RNDr. Miroslav Horváth PhD.100%100%100%
Mgr. Veronika Silliková100%100%-
Mgr. Paulína Galbavá100%100%100%
ISBN: 978-80-972360-1-4

Isatin hydrazones based on phenanthroline like skeleton – synthesis

Rastislav Ponický1 , Pavol Tisovský , Marek Cigáň , Anton Gáplovský
1 Chemický ústav Prírodovedecká fakulta Univerzity Komenského v Bratislave, Bratislava 4, Slovenská republika
rastislav.ponicky@gmail.com

This work deals with synthesis of new arylhydrazones with phenanthroline modification of isatin with application potential for various areas of supramolecular chemistry and photochemistry. The work describes preparation of basic phenanthroline isatin skeleton, namely 5H-pyrrolo [2,3-f] [1,10] phenanthroline-6,7-dione. The work consequently describes preparation of corresponding hydrazones as new molecular switches or colorimetric fluorescent/phosporescent chemosensors [1,2]. Presence of new phenantroline-like isatin skeleton ensures the light absorption in visible (close to infrared) region of electromagnetic spectrum. The presence of new phenantroline skeleton part in new hydrazones brings strong chelatation properties with important change of emission characteristics which can be modulated by photochemical switching around hydrazone C=N bond [3,4]. Implementation of an appropriate substituent to hydrazone phenyl moiety  can significantly influence interaction of hydrazones with anions and even the photochromism of these molecules. We have successfully prepared 5 for now undescribed derivatives, with the aim to find correlation between the structure and desired properties.

Poďakovanie: 

This publication was created thanks to support under the Operational Program Research and Innovation for the project: Comenius University College, Bratislava - 2nd Phase, ITMS 2014+ 313021D075, co-funded by the European Regional Development Fund.

Zdroje: 

 [1] Vantomme, G.; Lehn, J.M. Angew. Chem. Int. Ed. 2013, 52, 3940-3943. DOI:10.1002/anie.201210334.
 [2] Vantomme, G.; Lehn, J.M. Chem. Eur. J. 2014, 20, 1-7. DOI:10.1002/chem.201404561.
 [3] P. Alreja and N. Kaur, RSC Adv. 2016,6, 23169-23217. DOI: 10.1039/C6RA00150E.
 [4] Gianluca Accorsi, Andrea Listorti, K. Yoosaf and Nicola Armaroli, Chem. Soc. Rev. 2009, DOI: 10.1039/b806408n.

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