Self-assembly involving alkanediammonium ions and stereospecific [2+2] photocycloaddition of (18-crown-6)stilbene
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...
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Published in | Russian chemical bulletin Vol. 72; no. 3; pp. 740 - 748 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
New York
Springer US
01.03.2023
Springer Nature B.V |
Subjects | |
Online Access | Get full text |
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Summary: | 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. |
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ISSN: | 1066-5285 1573-9171 |
DOI: | 10.1007/s11172-023-3838-2 |