Excited state proton transfer in the Cinchona alkaloid cupreidine

Literature Information

Publication Date 2010-08-20
DOI 10.1039/C003419C
Impact Factor 3.676
Authors

Junhong Qian, Albert M. Brouwer


View Original

Abstract

Photophysical properties of the organocatalyst cupreidine (CPD) and its chromophoric building block 6-hydroxyquinoline (6HQ) in protic and nonprotic polar solvents (methanol and acetonitrile) were investigated by means of UV-vis absorption, and steady state and time resolved fluorescence spectroscopy. The effects of the catalytically relevant interactions with electrophilic and hydrogen bonding agents (p-toluene sulfonic acid and water) on their spectral characteristics were studied. In neutral CPD in acetonitrile, quenching of fluorescence occurs due to electron transfer from the quinuclidine nitrogen to the excited quinoline chromophore. Protonation suppresses this process, while complexation with water leads to enhanced excited state proton transfer from the 6′-OH group to the quinuclidine nitrogen, and emission occurs from the anionic form of the chromophore. The weakly emitting zwitterionic form of the hydroxyquinoline chromophore is readily formed in methanol, but not in acetonitrile.

Related Literature

Recent development of functional aliphatic polycarbonates for the construction of amphiphilic polymers

Yu Dai, Xiaojin Zhang

2017-11-09 Review Article

DOI: 10.1039/C7PY01815K

Inside front cover

Cover

DOI: 10.1039/C8PY90015A

Selective recognition of biologically important anions using a diblock polyfluorene–polythiophene conjugated polyelectrolyte

Niamh Willis-Fox, Andrea Gutacker, Michelle P. Browne, Amir R. Khan, Michael E. G. Lyons, Ullrich Scherf

2017-11-08 Paper

DOI: 10.1039/C7PY01478C

Electrochemically mediated ATRP in ionic liquids: controlled polymerization of methyl acrylate in [BMIm][OTf]

Francesco De Bon, Marco Fantin, Abdirisak A. Isse, Armando Gennaro

2018-01-09 Paper

DOI: 10.1039/C7PY02134H

Advances in polydiacetylene development for the design of side chain groups in smart material applications – a mini review

Jingpei Huo, Qianjun Deng, Ting Fan, Guozhang He, Xiaohong Hu, Xiaxiao Hong, Hong Chen, Shihe Luo, Zhaoyang Wang, Dongchu Chen

2017-10-25 Minireview

DOI: 10.1039/C7PY01396E

Thermo and pH dual-responsive drug-linked pseudo-polypeptide micelles with a comb-shaped polymer as a micellar exterior

Weizhi Chen, Liling Su, Peng Zhang, Cheng Li, Dan Zhang, Wei Wu, Xiqun Jiang

2017-10-17 Paper

DOI: 10.1039/C7PY01389B

Contents list

Front/Back Matter

DOI: 10.1039/C8PY90007H

Reactivity of self-assembled monolayers: formation of organized amino functionalities

Oliver Dannenberger, Klaus Weiss, Christof Wöll, Manfred Buck

2000-03-08 Paper

DOI: 10.1039/A909589F

You might also like

Compound Q&A

How is Ethyl 4-chlorothieno[2,3-b]pyridine-5-carboxylate (CAS: 59713-58-5) typically synthesized?

Ethyl 4-chlorothieno[2,3-b]pyridine-5-carboxylate (CAS: 59713-58-5) can be synth...

59713-58-5Ethyl 4-chlorothieno...
Compound Q&A

What regulatory guidelines apply to 5-Methyl-1H-indole-3-carbaldehyde (CAS: 52562-50-2)?

5-Methyl-1H-indole-3-carbaldehyde (CAS: 52562-50-2) is subject to various regula...

52562-50-25-Methyl-1H-indole-3...
Compound Q&A

What are the physical and chemical properties of (1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)boronic acid (CAS: 223418-73-3)?

(1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)boronic acid is a white...

223418-73-3(1,3-Dimethyl-2,4-di...
Compound Q&A

How should waste containing Sulfocostunolide A (CAS: 1016983-51-9) be handled?

Waste containing Sulfocostunolide A (CAS: 1016983-51-9) should be handled with c...

1016983-51-9Sulfocostunolide A
Compound Q&A

What precautions should be taken when handling Murraxocin (CAS: 88478-44-8)?

When handling Murraxocin (CAS: 88478-44-8), ensure proper personal protective eq...

88478-44-8Murraxocin
Compound Q&A

What are the physical and chemical properties of Formvar (CAS: 63148-64-1)?

Formvar (CAS: 63148-64-1) is an alkyd resin characterized by a high molecular we...

63148-64-1Formvar(R)
Compound Q&A

Is (S)-4-benzyl-2-((benzyloxy)methyl)morpholine (CAS: 205242-66-6) safe?

(S)-4-benzyl-2-((benzyloxy)methyl)morpholine is generally safe when handled with...

205242-66-6(S)-4-benzyl-2-((ben...
Compound Q&A

What industries use Methyl 1-(5-bromo-2-pyrimidinyl)cyclopropanecarboxylate (CAS: 1447607-69-3)?

Methyl 1-(5-bromo-2-pyrimidinyl)cyclopropanecarboxylate (CAS: 1447607-69-3) is p...

1447607-69-3Methyl 1-(5-bromo-2-...
Compound Q&A

Is 2-Methyl-1-phenyl-1-propanamine hydrochloride (CAS: 24290-47-9) safe?

2-Methyl-1-phenyl-1-propanamine hydrochloride (CAS: 24290-47-9) is generally con...

24290-47-92-Methyl-1-phenyl-1-...
Compound Q&A

How is 3-(4-Bromophenyl)-2-methylpropanoic acid (CAS: 66735-01-1) typically synthesized?

3-(4-Bromophenyl)-2-methylpropanoic acid is synthesized through a multi-step pro...

66735-01-13-(4-Bromophenyl)-2-...

Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.