Effect of Aromatic System Expansion on Crystal Structures of 1,2,5-Thia- and 1,2,5-Selenadiazoles and Their Quaternary Salts: Synthesis, Structure, and Spectroscopic Properties

Clicks: 111
ID: 267065
2020
Free PDF
Article Quality & Performance Metrics
Overall Quality
Not rated
Combines reader engagement with the AI quality analysis. This article has not been analysed, so there is no overall score — reader engagement is measured and shown alongside.
AI Quality Assessment
Not analyzed
Readership in this journal
Emerging

Ranked #713 of 812 articles by views in Materials (Basel, Switzerland)

Most read Least read

Bar heights use a square-root scale. Only the 120 most-read articles are drawn; the journal has 812 in total.

Mint this article as an NFT
Not yet minted

Create a permanent, verifiable on-chain record of this article on the Scimatic Network. The NFT is held in your Journament account, and you can withdraw it to your own wallet at any time.

5 SUSD one-off · no wallet required
Sign in to mint
Abstract
Rational manipulation of secondary bonding interactions is a crucial factor in the construction of new chalcogenadiazole-based materials. This article reports detailed experimental studies on phenanthro[9,10-c][1,2,5]chalcogenadiazolium and 2,1,3-benzochalcogenadiazolium salts and their precursors. The compounds were synthesized, characterized employing NMR and UV-Vis spectroscopy. TD-DFT calculations were also performed. The influence of the size of the aromatic system on the molecular motifs formed by the compounds in the solid state has been studied by means of single-crystal X-ray diffraction. In case of the salts, the nature of an anion was also taken into consideration. The results show that cyclic [E···N]2 supramolecular synthon connects neighboring molecules of phenanthro[9,10-c][1,2,5]chalcogenadiazoles, with a relatively large aromatic system, in dimers regardless of the chalcogen atom in the molecule. Both N-methyl-2,1,3-benzothiadiazolium and N-methylphenanthro[9,10-c][1,2,5]chalcogenadiazolium cations have a strong affinity for triflate and iodide anions, therefore the formation of S···N or Se···N secondary bonding interactions is observed only in two out of the eight quaternary salts. Less coordinating anions must be used to enable the building blocks studied to form cyclic [E···N]2 synthons. Moreover, for two of the triflate salts, which are isostructural, a new supramolecular motif has been observed.
Reference Key
alfuth2020materialseffect Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Jan Alfuth;Beata Zadykowicz;Artur Sikorski;Tadeusz Połoński;Katarzyna Eichstaedt;Teresa Olszewska;Alfuth, Jan;Zadykowicz, Beata;Sikorski, Artur;Połoński, Tadeusz;Eichstaedt, Katarzyna;Olszewska, Teresa;
Journal Materials (Basel, Switzerland)
Year 2020
DOI
10.3390/ma13214908
URL
https://doi.org/10.3390/ma13214908
Keywords
chalcogenadiazoles chalcogen bonds crystal engineering spectral properties

Citations

No citations found. To add a citation, contact the admin at info@scimatic.org

Comments

No comments yet. Be the first to comment on this article.