Details

Autor(en) / Beteiligte

• Koner, Kalipada
• Karak, Suvendu
• Ogaeri, Yutaro
• Nishiyama, Yusuke
• Banerjee, Rahul

Titel

Structural and Morphological Transformations of Covalent Organic Nanotubes

Ist Teil von

• Angewandte Chemie International Edition, 2023-05, Vol.62 (20), p.e202300652-n/a

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2023

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Covalent organic nanotubes (CONTs) are porous one‐dimensional frameworks connected through imine bonds via Schiff base condensation between aldehydes and amines. The presence of two amine groups at the ortho position in the structurally demanding tetraaminotriptycene (TAT) building block leads to multiple reaction pathways between the ditopic aldehyde and the tetratopic amine. We have synthesized five different monomers of CONT‐1 by the Schiff base condensation reaction between TAT and o‐anisaldehyde. The conversion of imine to imidazole bonding in a monomer is probed using NMR, mass spectrometry, and X‐ray diffraction techniques. Solid‐state NMR provide insights into the CONTs’ structural connectivity. A theoretical investigation suggests that the π‐π stacking could be the driving force for rapid imine to imidazole conversion within the CONT‐1. Microscopic imaging sheds further light on the self‐assembly process of the CONTs, indicating both head‐to‐head and side‐by‐side assembly. Two imine bonds at the ortho‐position of the benzene ring undergo a click rearrangement to form the imidazole ring. Two such geminal imine bonds in covalent organic nanotubes (CONTs) convert imine CONTs to imidazole CONTs. The CONTs exhibit two types of self‐assembly like gold nanorods, i.e., side‐by‐side assembly and head‐to‐head assembly.