Merging Triptycene, BODIPY and Porphyrin Chemistry: Synthesis and Properties of Mono‐ and Trisubstituted Triptycene Dye Arrays

A series of functionalized triptycene scaffolds has been synthesized using 2‐formyltriptycene and 5‐(2‐triptycenyl)dipyrromethane. Using these two key precursors, mixed condensations with different aromatic aldehydes and aryl‐dipyrromethanes gave access to all members of triptycenyl meso‐substituted...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-12, Vol.2017 (45), p.6680-6692
Main Authors: Emandi, Ganapathi, Shaker, Yasser M., Flanagan, Keith J., O'Brien, Jessica M., Senge, Mathias O.
Format: Article
Language:English
Subjects:
Aldehydes
Aromatic compounds
Arrays
Chemical reactions
Chemical synthesis
Cross coupling
Crystal structure
Dyes
Dyes/Pigments
Electrochemical analysis
Fluorescence
Functional organic materials
Porphyrinoids
Porphyrins
Scaffolds
Substitutes
Triptycene
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Summary:A series of functionalized triptycene scaffolds has been synthesized using 2‐formyltriptycene and 5‐(2‐triptycenyl)dipyrromethane. Using these two key precursors, mixed condensations with different aromatic aldehydes and aryl‐dipyrromethanes gave access to all members of triptycenyl meso‐substituted porphyrins (AB3‐, A2B2‐, A3B‐, and A4) and allowed their photophysical and electrochemical characterization. Additionally, the first crystal structure of tetratriptycenylporphyrin is reported. 2‐Formyltriptycene was also used for the preparation of two different mono‐BODIPY‐triptycene compounds, while 2,6,14‐triiodotriptycene was used in Suzuki and Sonogashira cross‐coupling reactions to obtain threefold BODIPY‐substituted triptycene–dye conjugates. The mono‐ and tri‐BODIPY‐substituted triptycene scaffolds exhibit good absorption in the visible to NIR region indicating the potential use of the triptycene scaffold as the core of multi‐dye light‐harvesting systems. A series of mono‐ and trisubstituted triptycene fluorescent dye arrays and triptycene‐appended porphyrins were synthesized and characterized by spectroscopic, crystallographic, and electrochemical techniques. These triptycene scaffolds can easily be modified with BODIPY or porphyrin units to yield dye arrays with high absorbance in the visible to NIR region.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201701206