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In 2,3,6,7,14,15\u2010hexaguanidino\u2010triptycenes, the three redox\u2010active <jats:italic>o<\/jats:italic>\u2010diguanidinobenzene units are connected through C\u2212C bonds to the sp<jats:sup>3<\/jats:sup>\u2010hybridized bridgehead C atoms, and in 2,3,6,7,10,11\u2010hexaguanidino\u2010triphenylenes they are directly connected. The connectivity difference leads to different electronic coupling between the three redox\u2010active <jats:italic>o<\/jats:italic>\u2010diguanidinobenzene units, with homoconjugation being present in the triptycene, but not in the triphenylene compounds. Motivated by the appearance of an intense low\u2010energy electronic transition, we especially analysed the effect of homoconjugation on the electronic structure and charge delocalization in the dicationic redox state of the triptycene derivatives. 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By choice of the coligands (hexafluoroacetylacetonate, trifluoroacetylacetonate and acetylacetonate), oxidation could be switched between metal\u2010 and ligand\u2010centered redox events, leading to drastic changes in the magnetic or optical properties, especially as a consequence of homoconjugation in the triptycene derivatives.<\/jats:p>","DOI":"10.1002\/chem.202301903","type":"journal-article","created":{"date-parts":[[2023,10,10]],"date-time":"2023-10-10T06:18:28Z","timestamp":1696918708000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Hexaguanidino\u2010Triptycenes and Triphenylenes: Electronic Coupling in Molecules Containing Three Redox\u2010Active <i>o<\/i>\u2010Diguanidinobenzene Units Connected either Directly or Interacting Through Homoconjugation"],"prefix":"10.1002","volume":"30","author":[{"given":"Sebastian","family":"Haaf","sequence":"first","affiliation":[{"name":"Inorganic Chemistry Ruprecht-Karls University Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Eliane","family":"Engels","sequence":"additional","affiliation":[{"name":"Inorganic Chemistry Ruprecht-Karls University Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elisabeth","family":"Kaifer","sequence":"additional","affiliation":[{"name":"Inorganic Chemistry Ruprecht-Karls University Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8111-3047","authenticated-orcid":false,"given":"Hans\u2010J\u00f6rg","family":"Himmel","sequence":"additional","affiliation":[{"name":"Inorganic Chemistry Ruprecht-Karls University Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,11,13]]},"reference":[{"key":"e_1_2_9_1_1","unstructured":"See for example: Organic Redox Systems Synthesis Properties \u2013Applications Ed. 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