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Sterically Allowed H-type Supramolecular Polymerizations
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DOI：10.1002/anie.202314211.png)
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摘要
En 中文
The functionalization of pi-conjugated scaffolds with sterically demanding substituents is a widely used tactic to suppress cofacial (H-type) stacking interactions, which may even inhibit self-assembly. Contrary to expectations, we demonstrate herein that increasing steric effects can result in an enhanced thermodynamic stability of H-type supramolecular polymers. In our approach, we have investigated two boron dipyrromethene (BODIPY) dyes with bulky phenyl (2) and mesityl (3) meso-substituents and compared their self-assembly in nonpolar media with that of a parent meso-methyl BODIPY 1 lacking bulky groups. While the enhanced steric demand induces pathway complexity, the superior thermodynamic stability of the H-type pathways can be rationalized in terms of additional enthalpic gain arising from intermolecular C-H & sdot;& sdot;& sdot;F-B interactions of the orthogonally arranged aromatic substituents, which overrule their inherent steric demand. Our findings underline the importance of balancing competing non-covalent interactions in self-assembly. Systematic increase in the bulkiness of dye substituents revealed an unexpected thermodynamic stability of face-to-face (H-type) stacking interactions during supramolecular polymerization. Our results contribute to the development of functional supramolecular polymers by controlling dye-dye interactions through molecular design.image
Keyword:
BODIPY Dyes
Pathway Complexity
Self-Assembly
Steric Effects
Supramolecular Polymorphism
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16.9
论文数:
5.7W
被引数:
53.0W
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