Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 23, Pages 15783-15795Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01758
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Funding
- Natural Sciences and Engineering Research Council of Canada [NFRFE-2018-00075]
- Canadian Tricouncil [ACS PRF 60765-ND7]
- American Chemical Society Petroleum Research Fund New Directions Program
- Oakland University, Michigan, USA
- [2018-06338]
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Mono-(bis)benzimidazoliums were evaluated for their potential as pseudopolyrotaxane axle building blocks through a combination of experimental and computational methods. Their aggregation and photophysical behavior were studied, revealing the potential to form pseudorotaxanes with tunable optical behavior.
Mono-and (bis)benzimidazoliums were evaluated both experimentally and computationally for their potential as pseudopolyrotaxane axle building blocks. Their aggregation and photophysical behavior, along with their potential to form a [2]pseudorotaxane with dibenzyl-24-crown-8, was studied through the synergistic application of 1D/2D and diffusion-ordered NMR spectroscopy, mass spectrometry, ultraviolet-visible and fluorescence spectroscopy, and time-dependent density functional theory. Their photophysical behavior was measured and modeled as a function of protonation state, solvent, and concentration. The axles show strong solvochromaticism and a very pronounced concentration-dependent optical profile, including self-quenching when a pseudorotaxane is formed. This axle with multiple recognition sites has the potential to form pseudorotaxanes with tunable optical behavior.
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