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CC BY-NC-ND 4.0 · Organic Materials 2019; 01(01): 050-062
DOI: 10.1055/s-0039-1700847
Original Article
The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/). (2019) The Author(s).

Triptycene End-Capped Quinoxalinophenanthrophenazines with Aromatic Substituents – Synthesis, Characterization, and Single-Crystal Structure Analysis

Lucas Ueberricke
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Email: Michael.mastalerz@oci.uni-heidelberg.de
,
Sonja Wieland
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Email: Michael.mastalerz@oci.uni-heidelberg.de
,
Frank Rominger
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Email: Michael.mastalerz@oci.uni-heidelberg.de
,
Michael Mastalerz 
a   Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Email: Michael.mastalerz@oci.uni-heidelberg.de
› Author Affiliations Funding Information Collaborative research center SFB1249 on N-heteropolycycles as functional materials funded by “Deutsche Forschungsgemeinschaft”.
Further Information

Publication History

03 July 2019

26 August 2019

Publication Date:
02 December 2019 (online)

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Abstract

In a previous study, we found that one-fold triptycene end-capped quinoxalinophenanthrophenazines (QPPs) arrange in crystals preferably in a coplanar fashion providing high overlap of the π-planes. Thus, resulting in high calculated charge transfer integrals. Most interestingly, this motif was observed for a variety of QPPs derivatives, independently of the nature of their peripheral substituents, e.g. bromide, methoxy, cyano, or triisopropylsilylethynyl groups, and of the crystallization conditions. Here, we describe the synthesis of another small series of three QPPs containing different aromatic substituents at the same position to get an insight, whether these aromatic substituents disturb the otherwise preferred π stacking of the QPP planes.

Key words

triptycenes - quinoxalinophenanthrophenazines - N-heterocycles - polycyclic aromatic compounds

Supporting Information

Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1700847.


Supporting Information