Journal
CHEMICAL SCIENCE
Volume 12, Issue 2, Pages 590-598Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc05067a
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Funding
- National Research Foundation (NRF) of Korea [2020R1A2C2006381, 2017M3D1A1039558]
- Ministry of Science and ICT
- National Research Foundation of Korea [2020R1A2C2006381, 2017M3D1A1039558] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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Hydrogen bonding-assisted polarization is an effective strategy in promoting specific chemical reactions. Through designing a unique platform structure with multiple hydrogen bonding donor and acceptor pairs, this study demonstrated that increased interdependent and strengthened hydrogen bonding contacts can significantly enhance reaction efficiency and selectivity.
Hydrogen bonding-assisted polarization is an effective strategy to promote bond-making and bond-breaking chemical reactions. Taking inspiration from the catalytic triad of serine protease active sites, we have devised a conformationally well-defined benzimidazole platform that can be systematically functionalized to install multiple hydrogen bonding donor (HBD) and acceptor (HBA) pairs in a serial fashion. We found that an increasing number of interdependent and mutually reinforcing HBD-HBA contacts facilitate the bond-forming reaction of a fluorescence-quenching aldehyde group with the cyanide ion, while suppressing the undesired Bronsted acid-base reaction. The most advanced system, evolved through iterative rule-finding studies, reacts rapidly and selectively with CN- to produce a large (>180-fold) enhancement in the fluorescence intensity at lambda(max) = 450 nm.
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