The Hairpin Furans: Easily Prepared Hybrids of Helicenes and Twisted Acenes

An unprecedented crystal-packing arrangement of at etramethoxy-bay-substituted perylene bisimide (PBI) consists of three crystallographically independent molecules,t hat is,anachiral (AC)PBI of saddle-shaped geometry along with two pairs of propeller-like twisted (P)-and (M)-enantiomeric PBI frameworks.A ll these five conformations are observed within as ingle p-stack revealing an intriguing packing sequence with an inversion of chirality from Pt oMvia AC. Nudged elastic band calculations for the isolated molecule show that AC is alocal minimum of the PtoMinterconversion path. In addition, two minor conformations were observed in the crystal, one of whichresembles atransition-state molecule. Theoretical studies of dimeric and trimeric stacks reveal that the coexistence of all these structures in the crystal lattice is aided by the strong dispersion interactions between PBI cores and perfectly interdigitated dodecyl chains which stabilize energetically higher conformations.

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A Crystalline π‐Stack Containing Five Stereoisomers: Insights into Conformational Isomorphism, Chirality Inversion, and Disorder

Nowak‐Król

Röhr

Schmidt

et al. 2017

Angewandte Chemie

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Catalyst‐Free Synthesis of O‐Heteroacenes by Ladderization of Fluorinated Oligophenylenes

et al. 2021

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A novel catalyst-free approach to benzoannulated oxygen-containing heterocycles from fluorinated oligophenylenes is reported. Unlike existing methods, the presented reaction does not require an oxygen-containing precursor and relies on an external oxygen source, potassium tertbutoxide, which serves as an O 2À synthon. The radical nature of the reaction facilitates nucleophilic substitution even in the presence of strong electron-donating groups and enables detert-butylation required for the complete annulation. Also demonstrated is the applicability of the method to introduce five-, six-, and seven-membered rings containing oxygen, whereas multiple annulations also open up a short synthetic path to ladder-type O-heteroacenes and oligodibenzofurans.

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A Crystalline π‐Stack Containing Five Stereoisomers: Insights into Conformational Isomorphism, Chirality Inversion, and Disorder

et al. 2017

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An unprecedented crystal-packing arrangement of a tetramethoxy-bay-substituted perylene bisimide (PBI) consists of three crystallographically independent molecules, that is, an achiral (AC) PBI of saddle-shaped geometry along with two pairs of propeller-like twisted (P)- and (M)-enantiomeric PBI frameworks. All these five conformations are observed within a single π-stack revealing an intriguing packing sequence with an inversion of chirality from P to M via AC. Nudged elastic band calculations for the isolated molecule show that AC is a local minimum of the P to M interconversion path. In addition, two minor conformations were observed in the crystal, one of which resembles a transition-state molecule. Theoretical studies of dimeric and trimeric stacks reveal that the coexistence of all these structures in the crystal lattice is aided by the strong dispersion interactions between PBI cores and perfectly interdigitated dodecyl chains which stabilize energetically higher conformations.

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The Hairpin Furans: Easily Prepared Hybrids of Helicenes and Twisted Acenes

Cited by 6 publications

References 18 publications

A Crystalline π‐Stack Containing Five Stereoisomers: Insights into Conformational Isomorphism, Chirality Inversion, and Disorder

A Crystalline π‐Stack Containing Five Stereoisomers: Insights into Conformational Isomorphism, Chirality Inversion, and Disorder

Catalyst‐Free Synthesis of O‐Heteroacenes by Ladderization of Fluorinated Oligophenylenes

A Crystalline π‐Stack Containing Five Stereoisomers: Insights into Conformational Isomorphism, Chirality Inversion, and Disorder

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