Structure, formation, thermodynamics and interactions in 9-carboxy-10-methylacridinium - based molecular systems

Damian Trzybiński , Beata Zadykowicz , Michał Wera , Illia Serdiuk , Andrzej Sieradzan , Artur Sikorski , Piotr Storoniak , Karol Krzymiński

Abstract

9-Carboxy-10-methylacridinium chloride and trifluoromethanesulfonate, the parent compounds for a wide range of chemiluminogenic salts of practical importance, were synthesized and thoroughly investigated to address problems concerning structural and thermodynamical issues of these cognitively interesting molecular systems. Under various conditions of crystallization, the title salts disclosed three types of crystals: one built from the monomeric form of cations and two containing homoconjugated cations. The title compounds made the first described derivatives of acridine, expressing homoconjugated cationic forms, both in crystalline solid and gaseous phases. The monocrystals were characterized, employing X-ray crystallography and spectroscopic methods such as MALDI-TOF MS, ESI-QTOF MS, NMR and UV-Vis. X-ray crystallography studies revealed the occurrence of the three different molecular architectures, in which not only the counter ions and stoichiometry are different, but also the space group and number of molecules in the unit cell. The energetics and intermolecular interactions occurring within the crystals were explored, applying crystal lattice energy calculations and Hirshfeld surface analysis. In order to elucidate the thermodynamics and origin of the experimentally revealed forms, computations based on the density functional theory were performed, assuming vapour and liquid phase.
Author Damian Trzybiński
Damian Trzybiński,,
-
, Beata Zadykowicz PBL
Beata Zadykowicz,,
- Laboratory of Luminescence Research
, Michał Wera KChF
Michał Wera,,
- Department of Physical Chemistry
, Illia Serdiuk IFD
Illia Serdiuk,,
- Institute of Experimental Physics
, Andrzej Sieradzan KChF
Andrzej Sieradzan,,
- Department of Physical Chemistry
, Artur Sikorski PK
Artur Sikorski,,
- Pracownia Krystalochemii
, Piotr Storoniak PSB
Piotr Storoniak,,
- Laboratory of Biological Sensitizers
, Karol Krzymiński PBL
Karol Krzymiński,,
- Laboratory of Luminescence Research
Journal seriesNew Journal of Chemistry, ISSN 1144-0546
Issue year2016
Vol40
Pages7359-7372
Publication size in sheets0.65
DOIDOI:10.1039/c6nj00725b
URL http://pubs.rsc.org/en/content/articlepdf/2016/nj/c6nj00725b
Languageen angielski
LicenseOther; published final; Uznanie Autorstwa - Użycie Niekomercyjne (CC-BY-NC); with publication
Score (nominal)30
ScoreMinisterial score = 30.0, 20-12-2017, ArticleFromJournal
Ministerial score (2013-2016) = 30.0, 20-12-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 3.269 (2) - 2016=3.103 (5)
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