G5 Doctoral dissertation (article)
Synthetic and structural studies on the effect of non-covalent interactions on N(sp²)-heterocyclic molecules (2022)
N(sp²)-heterosyklisten molekyylien vety- ja halogeenisitoutuneiden kompleksien synteettiset ja rakenteelliset tutkimukset

Taipale, E. (2022). Synthetic and structural studies on the effect of non-covalent interactions on N(sp²)-heterocyclic molecules [Doctoral dissertation]. University of Jyväskylä. JYU Dissertations, 496. http://urn.fi/URN:ISBN:978-951-39-9039-8

JYU authors or editors

Publication details

All authors or editors: Taipale, Essi

eISBN: 978-951-39-9039-8

Journal or series: JYU Dissertations

eISSN: 2489-9003

Publication year: 2022

Number in series: 496

Number of pages in the book: 1 verkkoaineisto (67 sivua, 34 sivua useina numerointijaksoina, 4 numeroimatonta sivua)

Publisher: University of Jyväskylä

Place of Publication: Jyväskylä

Publication country: Finland

Publication language: English

Persistent website address: http://urn.fi/URN:ISBN:978-951-39-9039-8

Publication open access: Openly available

Publication channel open access: Open Access channel

Abstract

The thesis herein describes the synthesis and characterization of compounds designed to be utilized as acceptor molecules in non-covalent interactions. The non-covalent interactions are applied in fluorescence modulation and construction of novel halogen-bonded complexes. In the literature part, an introduction to supramolecular chemistry and non-covalent interactions is given. It presents the concepts of light absorption and emission and discusses host-guest chemistry of larger supramolecular structures. At the end of the literature part, some common N(sp2)-heterocyclic molecules as hydrogen and halogen bond acceptor molecules are reviewed, highlighting the target compounds most relevant to the thesis work. The results and discussion part of the thesis describes the synthesis and characterization of imidazole- and carbazole-derived small-molecules as fluorescence emitters and hydrogen and halogen bond acceptors. The acceptor molecules were further utilized in the synthesis of larger tripodal N-donor ligands which were employed in the construction of halogen-bonded iodine(I) capsular assemblies manifesting three [N‒I‒N]+ three-center four-electron bonds through the intermediate silver(I) metallocage formation. The publication I focuses on the fundamentals of protonation and its potential in fluorescence modulation for simple, commercially available N(sp2)-heterocyclic molecules, viz. quinoline derivatives. This work was broadened in the publication II to carbazole derivatives. The publications III and IV focused on the development of small symmetric halogen-bonded iodine(I) carbazole complexes (publication III) and tris-imidazole based cage complexes (publication IV).

Keywords: halogens; heterocyclic compounds; hydrogen bonds; fluorescence; x-ray crystallography; supramolecular chemistry; doctoral dissertations

Free keywords: hydrogen bond; halogen bond; halogen(I) ions; halonium; iodonium; metallocage; supramolecular chemistry; non-covalent interactions; self-assembly; fluorescence; X-ray crystallography

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Related projects

Ministry reporting: Yes

VIRTA submission year: 2022