Femtosecond dynamics on 2-(2'-hydroxy-4'-diethylaminophenyl)benzothiazole: solvent polarity in the excited-state proton transfer

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
Yi-Ming ChengPi-Tai Chou

Abstract

Detailed insights into the excited-state enol(N*)-keto(T*) intramolecular proton transfer (ESIPT) reaction in 2-(2'-hydroxy-4'-diethylaminophenyl)benzothiazole (HABT) have been investigated via steady-state and femtosecond fluorescence upconversion approaches. In cyclohexane, in contrast to the ultrafast rate of ESIPT for the parent 2-(2'-hydroxyphenyl)benzothiazole (>2.9+/-0.3 x 10(13) s(-1)), HABT undergoes a relatively slow rate (approximately 5.4+/-0.5 x 10(11) s(-1)) of ESIPT. In polar aprotic solvents competitive rate of proton transfer and rate of solvent relaxation were resolved in the early dynamics. After reaching the solvation equilibrium in the normal excited state (N(eq)*), ESIPT takes place with an appreciable barrier. The results also show N(eq)*(enol)<-->T(eq)*(keto) equilibrium, which shifts toward N(eq)* as the solvent polarity increases. Temperature-dependent relaxation dynamics further resolved a solvent-induced barrier of 2.12 kcal mol(-1) for the forward reaction in CH(2)Cl(2). The observed spectroscopy and dynamics are rationalized by a significant difference in dipole moment between N(eq)* and T(eq)*, while the dipolar vector for the enol form in the ground state (N) is in between that of N(eq)* and T(eq...Continue Reading

References

Jan 30, 2003·Journal of the American Chemical Society·Matthew Lukeman, Peter Wan
Jun 13, 2003·Journal of Medicinal Chemistry·Chester A MathisWilliam E Klunk
Apr 1, 2005·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Abderrazzak DouhalJuan Angel Organero

❮ Previous
Next ❯

Citations

Mar 13, 2013·The Journal of Physical Chemistry. a·Nidhi SinglaPapia Chowdhury
Mar 19, 2013·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Rajib Ghosh, Dipak K Palit
Sep 30, 2008·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Cheng-Chih HsiehPi-Tai Chou
May 4, 2013·Chemistry : a European Journal·Kun CuiPaul J Dyson
Feb 22, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Fang GaoQi Wang
Dec 30, 2014·Photochemistry and Photobiology·Francis A S ChipemGovindarajan Krishnamoorthy
Apr 12, 2016·Chemistry : a European Journal·Kamil SkoniecznyDaniel T Gryko
Jun 13, 2015·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Noemí AlarcosAbderrazzak Douhal
Apr 15, 2015·Physical Chemistry Chemical Physics : PCCP·Noemí AlarcosAbderrazzak Douhal
Nov 22, 2012·Chemical Society Reviews·Alexander P DemchenkoPi-Tai Chou
Dec 20, 2014·The Journal of Physical Chemistry. B·Mario GutierrezAbderrazzak Douhal
Oct 18, 2013·The Journal of Physical Chemistry. B·Francis A S Chipem, Govindarajan Krishnamoorthy
Mar 16, 2017·Physical Chemistry Chemical Physics : PCCP·Tatu KumpulainenEric Vauthey
May 30, 2009·Journal of Computational Chemistry·Shihai YanJin Yong Lee
Oct 20, 2018·Physical Chemistry Chemical Physics : PCCP·Eduardo GomezAbderrazzak Douhal
Aug 20, 2008·The Journal of Physical Chemistry. a·Cheng-Chih HsiehPi-Tai Chou
Jan 6, 2010·The Journal of Physical Chemistry. a·Toshiyuki IijimaTatsuo Arai
Dec 7, 2011·The Journal of Physical Chemistry. a·Vikas S PatilNagaiyan Sekar
Dec 14, 2016·Chemical Reviews·Tatu KumpulainenEric Vauthey
Oct 24, 2017·The Journal of Physical Chemistry. B·Vikas S PadalkarShu Seki
Oct 20, 2010·Accounts of Chemical Research·Cheng-Chih HsiehPi-Tai Chou

❮ Previous
Next ❯

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.