A New Type of Excited-State Intramolecular Proton Transfer:  Proton Transfer from Phenol OH to a Carbon Atom of an Aromatic Ring Observed for 2-Phenylphenol1

2002 ◽  
Vol 124 (32) ◽  
pp. 9458-9464 ◽  
Author(s):  
Matthew Lukeman ◽  
Peter Wan
Keyword(s):  
Excited State ◽  
Carbon Atom ◽  
Proton Transfer ◽  
Aromatic Ring ◽  
Intramolecular Proton Transfer ◽  
New Type

Competing photodehydration and excited-state intramolecular proton transfer (ESIPT) in adamantyl derivatives of 2-phenylphenols

2011 ◽  
Vol 89 (2) ◽  
pp. 221-234 ◽  
Author(s):  
Nikola Basarić ◽  
Nikola Cindro ◽  
Yunyan Hou ◽  
Ivana Žabčić ◽  
Kata Mlinarić-Majerski ◽  
...  
Keyword(s):  
Excited State ◽  
Carbon Atom ◽  
Proton Transfer ◽  
Phenyl Ring ◽  
Flash Photolysis ◽  
Laser Flash Photolysis ◽  
Laser Flash ◽  
Intramolecular Proton Transfer ◽  
Hydroxyl Group ◽  
Quantum Yields

2-Phenylphenol derivatives strategically substituted with a hydroxyadamantyl substituent were synthesized and their photochemical reactivity was investigated. Derivatives 9 and 10 undergo competitive excited-state intramolecular proton transfer (ESIPT) from the phenol to the carbon atom of the adjacent phenyl ring and formal ESPT from the phenol to the hydroxyl group coupled with dehydration. These two processes (both via S1) give rise to two classes of quinone methides (QMs) that revert to starting material or react with nucleophiles, respectively. ESIPT to carbon atoms was studied by performing photolyses in the presence of D2O, whereupon deuterium incorporation to the adjacent phenyl ring was observed ([Formula: see text] = 0.1–0.2). The competing formal ESPT and dehydration takes place with quantum yields that are an order of magnitude lower and was studied by isolation of photomethanolysis products. Derivative 8 did not undergo ESIPT to carbon atom. Owing to the presence of an intramolecular H bond, an efficient ESIPT from the phenol to the hydroxyl group coupled with dehydration gives a QM that efficiently undergoes electrocyclization (overall [Formula: see text] = 0.33), to give chroman 16. In addition, spiro[adamantane-2,9′-(4′-hydroxy)fluorene] (12) undergoes ESIPT, unlike the previously reported unreactive parent 2-hydroxyfluorene. The reactive singlet excited states of the prepared biphenyl and fluorene molecules were characterized by fluorescence spectroscopy, whereas laser flash photolysis (LFP) was performed to characterize the longer lived QM intermediates.

Study of fluorescence probe transfer mechanism based on a new type of excited-state intramolecular proton transfer

2015 ◽  
Vol 144 ◽  
pp. 76-80 ◽  
Author(s):  
Yumei Dai ◽  
Jinfeng Zhao ◽  
Yanling Cui ◽  
Qianyu Wang ◽  
Peng Song ◽  
...  
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Fluorescence Probe ◽  
Intramolecular Proton Transfer ◽  
Transfer Mechanism ◽  
New Type

Ground and excited state intramolecular proton transfer controlled intramolecular charge separation and recombination: A new type of charge and proton transfer reaction

2008 ◽  
Vol 348 (1-3) ◽  
pp. 181-186 ◽  
Author(s):  
Daobo Nie ◽  
Zuqiang Bian ◽  
Anchi Yu ◽  
Zhuqi Chen ◽  
Zhiwei Liu ◽  
...  
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Charge Separation ◽  
Transfer Reaction ◽  
Proton Transfer Reaction ◽  
Intramolecular Proton Transfer ◽  
New Type

Very Efficient Generation of Quinone Methides through Excited State Intramolecular Proton Transfer to a Carbon Atom

2012 ◽  
Vol 18 (34) ◽  
pp. 10617-10623 ◽  
Author(s):  
Nikola Basarić ◽  
Nađa Došlić ◽  
Jakov Ivković ◽  
Yu-Hsuan Wang ◽  
Momir Mališ ◽  
...  
Keyword(s):  
Excited State ◽  
Carbon Atom ◽  
Proton Transfer ◽  
Intramolecular Proton Transfer ◽  
Quinone Methides ◽  
Efficient Generation

Proton transfer triggered proton transfer: a self-assisted twin excited state intramolecular proton transfer

2018 ◽  
Vol 20 (42) ◽  
pp. 27131-27139 ◽  
Author(s):  
Saugata Sahu ◽  
Minati Das ◽  
Aditya Kumar Bharti ◽  
G. Krishnamoorthy
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Intramolecular Proton Transfer ◽  
New Type

The double excited state intramolecular proton transfer (ESIPT) of 3,5-bis(2-hydroxyphenyl)-1H-1,2,4-triazole (bis-HPTA) has been investigated and found to undergo a new type of proton transfer.

The novel excited state intramolecular proton transfer broken by intermolecular hydrogen bonds in HOF system

2019 ◽  
Vol 219 ◽  
pp. 164-172 ◽  
Author(s):  
Songsong Liu ◽  
Yu Zhao ◽  
Changzhe Zhang ◽  
Lili Lin ◽  
Yongqing Li ◽  
...  
Keyword(s):  
Excited State ◽  
Hydrogen Bonds ◽  
Proton Transfer ◽  
Intramolecular Proton Transfer ◽  
The Novel ◽  
Intermolecular Hydrogen Bonds

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

Effect of nonproximate atomic substitution on excited state intramolecular proton transfer

1998 ◽  
Vol 19 (2) ◽  
pp. 129-138 ◽  
Author(s):  
Martin ?uma ◽  
Clifton Thompson ◽  
Steve Scheiner
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Intramolecular Proton Transfer ◽  
Atomic Substitution
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