Two Dimensional Triptycene End‐Capping and Its Influence on the Self‐Assembly of Quinoxalinophenanthrophenazines†

Abstract

Comprehensive SummaryIn this report we investigated two‐dimensionally triptycene end‐capped QPPs in terms of their solution and solid‐state behavior. For this purpose, a triphenylene based ortho‐diamine decorated with two triptycenyl units as well as a phenylene diamine with two non‐annulated triptycene units have been synthesized. Sequences of condensation reactions with a pyrene‐based tetraketone and ortho‐diamines yielded a series of QPPs and UV/Vis investigations of the corresponding compounds led to the conclusion, that the QPPs form dimers in solution, which was further supported by MALDI‐TIMS‐TOF‐MS. Single‐crystal X‐ray analysis of the triply and quadruply triptycene end‐capped QPPs furthermore showed short π‐π‐distances of 3.3—3.4 Å and a perfect shape match during the dimerization of the triply triptycenyl end‐capped QPP making it possible synthon for crystal engineering.