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Review

Syntheses, Structures and Reactivity of Metal Complexes of Trindane, Trindene, Truxene, Decacyclene and Related Ring Systems: Manifestations of Three-Fold Symmetry

by
Philippa E. Lock
,
Nada Reginato
,
Julia Bruno-Colmenárez
and
Michael J. McGlinchey
*
School of Chemistry, University College Dublin, Belfield, D04 V1W8 Dublin, Ireland
*
Author to whom correspondence should be addressed.
Molecules 2023, 28(23), 7796; https://doi.org/10.3390/molecules28237796
Submission received: 24 October 2023 / Revised: 20 November 2023 / Accepted: 23 November 2023 / Published: 27 November 2023
(This article belongs to the Section Organometallic Chemistry)
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Abstract

The triple condensation of cyclopentanone or indanone to trindane (C15H18) or truxene (C27H18), respectively, provides convenient access to molecular skeletons on which major fragments of the prototypical fullerene C60 can be assembled. In particular, early approaches (both organic and organometallic) towards sumanene, as well as the final successful synthesis, are described. Organometallic derivatives of trindane have been prepared in which Cr(CO)3, Mo(CO)3, [Mn(CO)3]+ or [(C5H5)Fe(CO)2]+ are η6-bonded to the central arene ring. The debromination of hexabromotrindane yields trindene, which forms a tri-anion to which as many as three organometallic fragments, such as Mn(CO)3, W(CO)3Me, or Rh(CO)2, may be attached. Truxene forms complexes whereby three metal fragments can bind either to the peripheral arene rings, or to the five-membered rings, and these can be interconverted via η6 ↔ η5 haptotropic shifts. Truxene also forms a double-decker sandwich with Ag(I) bridges, and decacyclene, C36H18, forms triple-decker sandwiches bearing multiple cyclopentadienyl-nickel or -iron moieties. The organic chemistry of trindane has been investigated, especially with respect to its unexpectedly complex oxidation products, which were only identified unambiguously via X-ray crystallography. The three-fold symmetric trindane framework has also been used as a template upon which a potential artificial receptor has been constructed. Finally, the use of truxene and truxenone derivatives in a wide range of applications is highlighted.
Keywords: ketone triple condensations; polycyclic frameworks; metal π-complexes; C60 fragments; three-fold symmetry; X-ray crystallography ketone triple condensations; polycyclic frameworks; metal π-complexes; C60 fragments; three-fold symmetry; X-ray crystallography

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MDPI and ACS Style

Lock, P.E.; Reginato, N.; Bruno-Colmenárez, J.; McGlinchey, M.J. Syntheses, Structures and Reactivity of Metal Complexes of Trindane, Trindene, Truxene, Decacyclene and Related Ring Systems: Manifestations of Three-Fold Symmetry. Molecules 2023, 28, 7796. https://doi.org/10.3390/molecules28237796

AMA Style

Lock PE, Reginato N, Bruno-Colmenárez J, McGlinchey MJ. Syntheses, Structures and Reactivity of Metal Complexes of Trindane, Trindene, Truxene, Decacyclene and Related Ring Systems: Manifestations of Three-Fold Symmetry. Molecules. 2023; 28(23):7796. https://doi.org/10.3390/molecules28237796

Chicago/Turabian Style

Lock, Philippa E., Nada Reginato, Julia Bruno-Colmenárez, and Michael J. McGlinchey. 2023. "Syntheses, Structures and Reactivity of Metal Complexes of Trindane, Trindene, Truxene, Decacyclene and Related Ring Systems: Manifestations of Three-Fold Symmetry" Molecules 28, no. 23: 7796. https://doi.org/10.3390/molecules28237796

APA Style

Lock, P. E., Reginato, N., Bruno-Colmenárez, J., & McGlinchey, M. J. (2023). Syntheses, Structures and Reactivity of Metal Complexes of Trindane, Trindene, Truxene, Decacyclene and Related Ring Systems: Manifestations of Three-Fold Symmetry. Molecules, 28(23), 7796. https://doi.org/10.3390/molecules28237796

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