AI Article Synopsis
- - Pentacosacyclene (PC) and its derivative pentacosacyclene tetraimide (PCTI) were synthesized from tridecacyclene, with PC being electron-rich and PCTI being electron-deficient.
- - Both compounds exhibit non-planar saddle shapes, with PC capable of forming a unique supramolecular crystal phase in combination with carbon (C) atoms.
- - PCTI undergoes multiple single-electron reductions in solution, while PC shows various reversible redox reactions; their varying electronic properties can be explained through molecular orbital theories related to the structure of their cyclic rings.
Article Abstract
Pentacosacyclene (PC) and pentacosacyclene tetraimide (PCTI) were obtained in concise syntheses involving radial extension of tridecacyclene. PC is an electron-rich hydrocarbon with a C π-conjugated framework, whereas PCTI is electron-deficient and contains a CN core. PC and PCTI both have non-planar saddle-shaped conformations, and PC was found to self-assemble with C to produce a uniquely structured supramolecular crystalline phase. In solution, PCTI undergoes eight single-electron reductions, while PC exhibits two reversible oxidations and three reversible reduction events. Chemically generated anions of PC and PCTI showcase extended near-infrared to infrared absorptions, with the lowest energy bands observed at >3200 nm for the PCTI monoanion and 2800 nm for the PCTI dianion. The electronic and redox properties of pentacosacyclenes can be explained using molecular orbital and valence bond theories as originating from changes in the local aromaticity of five- and eight-membered rings.
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Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11499954 | PMC |
| http://dx.doi.org/10.1039/d4sc05938g | DOI Listing |
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