Molecular Recognition and Chemical Sensing of Anions Utilizing Excited-State Hydrogen-Bonding Interaction

2010 ◽  
pp. 805-814 ◽  
Author(s):  
Ashutosh S. Singh ◽  
Shih-Sheng Sun
Keyword(s):  
Hydrogen Bonding ◽  
Excited State ◽  
Molecular Recognition ◽  
Chemical Sensing ◽  
Hydrogen Bonding Interaction ◽  
Bonding Interaction

Solid-State Photocycloaddition Reactions between Di-2-Pyrones Tethered by Arylalkyl Chain and Benzophenones

2011 ◽  
Vol 396-398 ◽  
pp. 2467-2470
Author(s):  
Wei Dong Wang ◽  
Tetsuro Shimo
Keyword(s):  
Hydrogen Bonding ◽  
Excited State ◽  
Reaction Mechanism ◽  
Solid State ◽  
Carbonyl Oxygen ◽  
Hydrogen Bonding Interaction ◽  
Triplet Excited State ◽  
Bonding Interaction ◽  
High Site ◽  
Solid State Interaction

Solid-state photocycloaddition reactions between di-2-pyrones (1a-d) with benzophenone (2a) gave the corresponding oxetane derivatives (3a-d; 1:2 adducts) with high site- and regioselectivity across the C5-C6 and C5′-C6′ double bonds in 1 via the triplet excited state of 2a. The reactions were inferred by MO methods to be initiated by electrostatic interaction between the C6 position of 1a-d and the carbonyl oxygen of 2a at their ground states, and the solid-state interaction may be enhanced by electron density at carbonyl oxygen of the triplet 2a. The transition state (TS) analysis of the [2+2] cycloaddition reactions also suggested some triplet complex, and the high regioselectivity. The hydrogen-bonding interaction between 2a and 1a-d and the triplet reaction mechanism were also explained by the IR analyses and the quenching experiments, respectively.

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