Investigations into an Intramolecular Proton Transfer and Solvent Dependent Acid‐Base Equilibria in 2,6‐Pyridine Diacetic Acid

2019 ◽  
Vol 4 (14) ◽  
pp. 4301-4307 ◽  
Author(s):  
Shivani Boodram ◽  
Soumyabrata Roy ◽  
Nadia Singh ◽  
Richard A. Fairman ◽  
Sebastian C. Peter ◽  
...  
Keyword(s):  
Proton Transfer ◽  
Intramolecular Proton Transfer ◽  
Diacetic Acid ◽  
Acid Base

Excited state intramolecular proton transfer in 1-hydroxypyrene

2011 ◽  
Vol 89 (3) ◽  
pp. 433-440 ◽  
Author(s):  
Matthew Lukeman ◽  
Misty-Dawn Burns ◽  
Peter Wan
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Intramolecular Proton Transfer ◽  
Quinone Methide ◽  
Acid Base ◽  
Quinone Methides ◽  
Marked Enhancement ◽  
Theoretical Predictions ◽  
Important Pathway ◽  
Acetonitrile Solutions

1-Hydroxypyrene (1) shows unusual acid–base chemistry in its singlet excited state. Whereas most hydroxyarenes experience a marked enhancement in their acidity when excited, and rapidly deprotonate to give the corresponding phenolate anion, this is not an important pathway for 1, despite theoretical predictions that 1 should experience enhanced acidity as well. In this work, we demonstrate that 1 undergoes a competing excited state intramolecular proton transfer from the OH to carbon atoms at the 3, 6, and 8 positions of the pyrene ring to give quinone methide intermediates. When the reaction is carried out in D2O, reversion of these quinone methides to starting material results in replacement of the ring hydrogens with deuterium, providing a convenient handle to follow the reaction with NMR spectroscopy and mass spectrometry. The quantum yield for the reaction is 0.025 and appears to not be strongly dependent on the water content when aqueous acetonitrile solutions are used. 1-(2-Hydroxyphenyl)pyrene (19) was prepared and studied and shows similar reactivity to 1.

scholarly journals An enhanced sampling QM/AMOEBA approach: The case of the excited state intramolecular proton transfer in solvated 3-hydroxyflavone

2021 ◽  
Vol 154 (18) ◽  
pp. 184107
Author(s):  
Michele Nottoli ◽  
Mattia Bondanza ◽  
Filippo Lipparini ◽  
Benedetta Mennucci
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Intramolecular Proton Transfer ◽  
Enhanced Sampling

scholarly journals The development of aryl-substituted 2-phenylimidazo[1,2-a]pyridines (PIP) with various colors of excited-state intramolecular proton transfer (ESIPT) luminescence in the solid state

2016 ◽  
Vol 4 (16) ◽  
pp. 3599-3606 ◽  
Author(s):  
Toshiki Mutai ◽  
Tatsuya Ohkawa ◽  
Hideaki Shono ◽  
Koji Araki
Keyword(s):  
Excited State ◽  
Solid State ◽  
Proton Transfer ◽  
Intramolecular Proton Transfer ◽  
Aryl Group ◽  
Red Emission ◽  
Wide Range

The color of ESIPT luminescence of HPIP is tuned in a wide range by the introduction of aryl group(s), and thus a series of PIPs showing blue to red emission is realized.

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