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Dr. Peter Wan
Professor
Ph.D. 1983,
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Mechanistic
Organic Photochemistry; Excited State Proton Transfer
Photoinduced Redox Reactions;
Environmental Organic Photochemistry
(dioxins; PCBs); Molecular Photoswitching
Systems
Organic photochemistry is a branch of organic chemistry that studies
light-induced chemical reactions of organic compounds. Many relevant organic photochemical reactions
are found in nature. The vision process utilizes a photochemical cis-trans isomerization of a polyene; the photochemical synthesis of vitamin D in
mammals is initiated by a photochemical 6pi electrocyclic
ring opening of a cyclohexadiene unit. In most
instances, the reactions displayed by excited state organic molecules have no
ground state (i.e. thermal) analogs.
Dr. Wan's research is directed towards understanding fundamental reactions of organic molecular
systems in electronically excited states via physical organic, classical
photochemical (including steady-state and time-resolved luminescence
techniques) and laser flash photolysis. Reactions of current interest
involve excited state proton and charge transfer processes that have been
discovered in our laboratory in recent years, resulting in new types of
photochemical reactions. Other systems of interest involve quinone methides, carbocations and carbanions. Although the majority of the reactions
studied are carried out in solution, some compounds of interest also react in
the solid state.
Students in Dr.
Wan's group design and synthesize a wide range of organic compounds for
photochemical study. Therefore, students are exposed to techniques in
preparative organic chemistry as well as standard and state-of-the-art
techniques in photochemistry and photophysics.
Modern materials science also requires a good understanding of how light
interacts with organic materials. Students from Dr. Wan's
group are trained at the fundamental level to fully appreciate and carry out
research in areas of material science where light is used (as a
"switch" or for information transfer).
In addition to the
projects described above, where either the M.Sc. or Ph.D. program may be
pursued, Dr. Wan is also accepting M.Sc. or Ph.D. students interested in the photochemical transformation of relevant
trace organic pollutants in the environment. This work will involve
aspects of environmental analytical
chemistry as well as mechanistic organic photochemistry. These
projects will be carried out in collaboration with the Applied Environmental Research Laboratory (AERL)
at
Recent Publications:
(133) N. Basarić, A. Franco-Cea, M. Alešković, K. Mlinarić-Majerski and P. Wan, Photochemical Deuterium Exchange in Phenyl-Substituted Pyrroles and Indoles in CD3CN-D2O, Photochem. Photobiol. Sci., 2010, submitted.
(132) N. Basarić, I. Žabčić, K. Mlinarić-Majerski and P. Wan, Photochemical Formation and Chemistry of Long-lived Adamantyl-Quinone Methides and 2-Adamantyl Cations, J. Org. Chem., 2010, 75, 102-116.
(131) N. Behin Aein and P. Wan, Excited
State Intramolecular Proton Transfer (ESIPT) from
Phenol OH (OD) to Adjacent “Aromatic” Carbons in Simple Biphenyls,
J. Photochem. Photobiol. A, 2009, 208,
42-49.
(130) Y. Hou, L. A.
Huck and P. Wan, Long-Range Intramolecular Photoredox
Reaction via Coupled Charge and Proton Transfer of Triplet Excited Anthraquinones Mediated by Water, Photochem.
Photobiol.
Sci., 2009, 8, 1408-1415.
(129) E. Dallin, P. Wan, E. Krogh, C. Gill and R. M. Moore, New pH-Dependent Photosubstitution Pathways of Syringic Acid in Aqueous Solution: Relevance in Environmental Photochemistry, J. Photochem. Photobiol. A, 2009, 207, 297-305.
(128) D. Mitchell and P. Wan, Formal Intramolecular Photoredox Reactions of Phenylbenzophenones, Xanthone and Fluorenone Methanols in Aqueous Solution, J. Photochem. Photobiol. A, 2009, 205, 34-43.
(127) M. Xu, M. Lukeman and P. Wan, Photodecarboxylation of Benzoyl-Substituted Biphenylacetic Acids and Photo-Retro-Aldol Reaction of Related Compounds in Aqueous Solution. Acid and Base Catalysis of Reaction, J. Photochem. Photobiol. A, 2009, 204, 52-62.
(126) M. K. Nayak and P. Wan, Direct and Water-Mediated Excited State Intramolecular Proton Transfer (ESIPT) from Phenol OH to Carbon Atoms of Extended ortho-Substituted Biaryl Systems, Photochem. Photobiol. Sci., 2008, 7, 1544-1554.
(125) M. Xu, C. Z. Chen and P. Wan, Intramolecular Charge Transfer in Photoexcited Hydroxyterphenyls: Evidence for Formation of Terphenyl Quinone Methides in Aqueous Solution, J. Photochem. Photobiol. A, 2008, 198, 26-33.
(124) Y. Hou and P.
Wan, Formal Intramolecular Photoredox Chemistry of Anthraquinones in Aqueous Solution: Photodeprotection
for Alcohols, Aldehydes and Ketones,
Photochem. Photobiol. Sci., 2008, 7,
588-596.
(123) M. Flegel, M. Lukeman, and P. Wan, Photochemistry of 1,1’-Bi-2-Naphthol (BINOL) – ESIPT is Responsible for Photoracemization and Photoocyclization, Can. J. Chem., 2008, 86, 161-169.
(122) L. Diao and P. Wan, Chemistry of Photogenerated a-Phenyl-Substituted o-, m- and p-Quinone Methides from Phenol Derivatives in Aqueous Solution, Can. J. Chem., 2008, 86, 105-118.
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