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Towards Triptycene Functionalization and Triptycene-linked Porphyrin Arrays

preprint
submitted on 07.01.2020, 18:40 and posted on 09.01.2020, 16:31 by Gemma Locke, Keith Flanagan, Mathias Senge
9,10-Diethynyltriptycene is investigated for its use as a rigid isolating unit in the synthesis of multichromophoric arrays. Sonogashira cross-coupling conditions are utilized to attach various porphyrins and boron dipyrromethenes (BODIPYs) to the triptycene scaffold. While there are previous examples of triptycene porphyrin complexes, this work reports the first example of a linearly connected porphyrin dimer, linked through the bridgehead carbons of triptycene. Symmetric and unsymmetric examples of these complexes are demonstrated and single crystal X-ray analysis of an unsymmetrically substituted porphyrin dimer highlights the evident linearity in these systems. Moreover, initial UV-Vis and fluorescence studies show the promise of triptycene as a linker for electron transfer studies, showcasing its isolating nature

Funding

Science Foundation Ireland (SFI IvP 13/IA/1894)

Irish Research Council (GOIPG/2015/3700)

History

Email Address of Submitting Author

tetrapyrroles@gmx.de

Institution

Trinity College Dublin, The University of Dublin

Country

Ireland

ORCID For Submitting Author

0000-0002-7467-1654

Declaration of Conflict of Interest

The authors declare no conflict of interest.

Version Notes

Version 1.0

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