Self-assembly involving alkanediammonium ions and stereospecific [2+2] photocycloaddition of (18-crown-6)stilbene

• Published in: Russian chemical bulletin Vol. 72; no. 3; pp. 740 - 748
• Main Authors: Martyanov, T. P., Vorozhtsov, A. P., Aleksandrova, N. A., Sulimenkov, I. V., Slesarenko, N. A., Ushakov, E. N., Gromov, S. P.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.03.2023; Springer Nature B.V
• Subjects: Alkanes; Chemical reactions; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Cyclobutane; Full Articles; Inorganic Chemistry; Methylene; NMR spectroscopy; Organic Chemistry; Phenanthrene; Photolysis; Self-assembly; Stilbene; photocycloaddition; stilbene; self-assembly; cyclobutane; crown ether
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-023-3838-2

Complexation between (18-crown-6)stilbene and alkanediammonium ions + H 3 N(CH 2 ) n NH 3 + ( n = 2−4) resulting in the pseudo-sandwich 2:1 stilbene—dication complexes and 1:1 stilbene—dication complexes was studied by NMR spectroscopy. The stability of the complexes decreases as the methylene chain length in the alkanediammonium ion increases. UV photolysis of the bis-ligand complexes produces two major products, viz. , the rctt isomer of a biscrown-containing cyclobutane derivative formed as a result of intra-supramolecular [2+2] photocycloaddition and a crown-containing phenanthrene derivative (product of electrocyclization reaction). The effective quantum yields of both cyclization reactions occurring in the pseudo-sandwich complexes increase as the number of methylene units in the dication decreases.