Paul Bonvallet: College of Wooster Department of Chemistry

Paul Bonvallet Research Page

Paul A. Bonvallet, Assistant Professor
Department of Chemistry
College of Wooster
943 College Mall
Wooster, OH 44691

Telephone: 330-263-2610
FAX: 330-263-2386
E-mail: pbonvallet@wooster.edu

Photo by Matt Dilyard

Research Interests

The most up-to-date synopsis for students can be found here:
Description of potential CHEMISTRY Senior I.S. projects for 2008-2009 (PDF, Jan 2008)
Description of potential BMB Senior I.S. projects for 2008-2009 (PDF, Jan 2008)
Presentation to the junior class for potential Senior I.S. projects (PowerPoint, Jan 2008)

1. Supramolecular Chemistry

Investigation of "host-guest" complexes held together and organized by noncovalent interactions such as hydrogen bonding, pi-pi stacking, and van der Waals forces. Mechanically interlocked structures such as rotaxanes and catenanes can be constructed via template-directed synthesis.

A. "Host-Guest" Chemistry


B. Photo-reactive Molecular Container


C. Encapsulation of Drugs with Cyclodextrins

2. Light-emitting Polymers / Organic Light Emitting Diodes (OLEDs)

Synthesis and characterization of conjugated polymers capable of emitting light when photoexcited (photoluminescence) or between two electrodes (electroluminescence).

3. Reactive Organic Intermediates

Computational and experimental investigation of the structure and reactivity of 9-tryptycylcarbene

Research Personnel
(* indicates Senior Independent Study advisee)

	Student	Project Title and/or Current Position
18.	Andrew Marley '10	Chemistry/Archaeology major
17.*	Paul Evans '08	Chemistry major
16.*	Joel Keelor '08	Chemistry major
15.*	Richard Giles '07	Benzylic Bromination of a Key Synthetic Precursor to a Conjugated Crown Ether-Substituted Polymer Graduate student, University of Southern California (Chemistry)
14.*	Brian Ondrusek '07	Synthesis of the Monomeric Components of a Polyfluorene Copolymer with Pyrene End-caps
13.*	Katie Wieferich '07	An Investigation of the Effects of Statins on Exercise Capacity, with a Subsequent Study of the Use of Creatine as a Potential Intervention
12.*	Benjamin Williams '07	Blinded by the Light: Development of Organic Light-Emitting Diode Fabrication Techniques in the Pursuit of Examining Device Properties
11.	Valerie Andrus '09	BMB major
10.*	Erin Fortin '08	Chemistry major
9.	Benjamin Franks '08	Chemistry major
8.	Marisa McGinley '08	BMB major
7.	David Thomas '07	BMB major
6.*	Anna (Maria) Holdcroft '06	Glowing Devices: Fabrication of a Functional, Single-Layer Organic Light-Emitting Diode Using a Non-Traditional Metal Cathod and Three Light-Emitting Materials Graduate student, University of Kentucky (Plant Pathology)
5.*	Nathan Little '06	Computational Investigation of the Structure, Energy and Reactivity of 9-Tryptycylcarbene Chemist for Martel Laboratories (environmental testing company in Baltimore, MD) Link to Martel Laboratories Web site
4.*	Josephine Sasu-Tenkoramaa '06	Progress Toward the Synthesis of a Poly(para-Phenylenevinylene) Derivative Substituted with Dibenzo-30-Crown-10 Research chemist, Merck Research Labs Link to MRL Web site
3.*	Erica Shubeck '06	Progress Towards Synthesizing a Dimeric Calix[4]arene Molecular Container Researcher for Promerus (electronic materials company in Brecksville, OH.) Link to Promerus Web site
2.*	Adam Milligan '05	Investigating the Complexation of Benzyl Viologen and Dibenzo-30-crown-10 Ether as a Basis for the Color Tuning of a Conducting Polymer Law student (University of Toledo) View Adam's scoring records on the Wooster soccer team.
1.*	Daniel Skully '05	Progress Toward the Synthesis of a Model Electroluminescent Polymer Medical student (Ohio State University) See Dan Skully breaking boards with various body parts.

Research Support

"Acquisition of an Isothermal Titration Calorimeter," Paul A. Bonvallet (PI), Mark J. Snider, Donald Jacobs (co-PIs), Judith Amburgey-Peters (Senior Personnel); National Science Foundation / Major Research Instrumentation ($91,090).

"The Synthesis, Characterization, and Supramolecular Properties of a Light-Emitting Polymer," Paul A. Bonvallet; Research Corporation Cottrell College Science Award ($36,232).

Peer-Reviewed Publications

10.	Bonvallet, P. A.; Breitkreuz, C. J.; Kim, Y. S.; Todd, E. M.; Traynor, K.; Fry, C. G.; Ediger, M. D.; McMahon, R. J. Organic Glass-Forming Materials: 1,3,5-Tris(naphthyl)benzene Derivatives. J. Org. Chem. (in press).
9.	Huang, T. J.; Flood, A. H., Brough, B.; Liu, Y., Bonvallet, P. A.; Kang, S.; Chu, C.-W.; Guo, T. F.; Lu, W.; Yang, Y.; Stoddart, J. F.; Ho, C.-M. Understanding and Harnessing Biomimetic Molecular Machines for NEMS Actuation Materials. IEEE Trans. Autom. Sci. Eng. (special issue on nanoscale automation and assembly) 2006, 3, 254-259.
8.	Liu, Y.; Vignon, S. A.; Zhang, X.; Bonvallet, P. A.; Kahn, S. I.; Houk, K. N.; Stoddart, J. F. Dynamic Chirality in Donor-Acceptor Pretzelanes. J. Org. Chem. 2005, 70, 9334-9344.
7.	Liu, Y.; Flood, A. H.; Bonvallet, P. A.; Vignon, S. A.; Northrop, B. H.; Tseng, H.-R.; Jeppesen, J. O.; Huang, T. J.; Brough, B.; Baller, M.; Magonov, S.; Solares, S. D.; Goddard, W. A.; Ho, C.-M.; Stoddart, J. F. Linear Artificial Molecular Muscles. J. Am. Chem. Soc. 2005, 127, 9745-9759.
6.	Liu, Y.; Bonvallet, P. A.; Vignon, S. A.; Kahn, S. I.; Stoddart, J. F. Donor-Acceptor Pretzelanes and a Cyclic Bis[2]Catenane Homologue. Angew. Chem., Int. Ed. 2005, 44, 3050-3055.
5.	Huang, T. J.; Brough, B.; Ho, C.-M.; Liu, Y.; Flood, A. H.; Bonvallet, P. A.; Tseng, H.-R.; Stoddart, J. F.; Baller, M.; Magonov, S. A nanomechanical device based on linear molecular motors (cover story). Appl. Phys. Lett. 2004, 85, 5391-5393.
4.	Swallen, S. F.; Bonvallet, P. A.; McMahon, R. J.; Ediger, M. D. Self-Diffusion of tris-Naphthylbenzene Near the Glass Transition Temperature. Phys. Rev. Lett. 2003, 90, 015901/1-015901/4.
3.	Bonvallet, P. A.; Todd, E. M.; Kim, Y. S.; McMahon, R. J. Access to the Naphthylcarbene Rearrangement Manifold via Isomeric Benzodiazocycloheptatrienes. J. Org. Chem. 2002, 67, 9031-9042.
2.	Bonvallet, P. A.; McMahon, R. J. Generation, Characterization, and Rearrangements of 4,5 Benzocyclohepta-1,2,4,6-tetraene. J. Am. Chem. Soc. 2000, 122, 9332-9333.
1.	Bonvallet, P. A.; McMahon, R. J. Photoequilibration of 1-Naphthylcarbene and 4,5-Benzobicyclo[4.1.0]hepta-2,4,6-triene. J. Am. Chem. Soc. 1999, 121, 10496-10503.

Published Conference Abstracts

12. Bonvallet, P. A.; Amburgey-Peters, J. C. Casting away the cookbook: Bringing independent experimental design into an organic chemistry laboratory experiment. Abstracts of Papers, 233rd National Meeting of the American Chemical Society, Chicago, IL, Mar 25-29, 2007; CHED 390.

11. Andrus, V. M.;‡ Thomas, D. H.;‡ Bonvallet, P. A. Synthesis of a nitro-substituted crown ether for incorporation into a light-emitting polymer. Abstracts of Papers, 233rd National Meeting of the American Chemical Society, Chicago, IL, Mar 25-29, 2007; CHED 703.

10. Fortin, E. E.;‡ Bonvallet, P. A. Synthesis and characterization of a dimethyl dibenzo-30-crown-10 ether. Abstracts of Papers, 233rd National Meeting of the American Chemical Society, Chicago, IL, Mar 25-29, 2007; CHED 682.

9. Franks, B. A.;‡ Bonvallet, P. A. Investigation of the Horner-Wadsworth-Emmons reaction for the preparation of a conjugated polymer. Abstracts of Papers, 233rd National Meeting of the American Chemical Society, Chicago, IL, Mar 25-29, 2007; CHED 596.

8. Giles, R. A.;‡ Skully, D. F.;‡ Bonvallet, P. A. Synthesis of a conjugated photoluminescent polymer. Abstracts of Papers, 231st National Meeting of the American Chemical Society, Atlanta, GA, Mar 26-30, 2006; CHED 524.

7. McGinley, M. P.;‡ Bonvallet, P. A. Photoluminescence of supramolecular systems for a proposed organic light-emitting diode. Abstracts of Papers, 231st National Meeting of the American Chemical Society, Atlanta, GA, Mar 26-30, 2006; CHED 458.

6. Thomas, D. H.;‡ Milligan, A. C.;‡ Bonvallet, P. A. Spectroscopic analysis of supramolecular complexes for use in organic light-emitting diodes. Abstracts of Papers, 231st National Meeting of the American Chemical Society, Atlanta, GA, Mar 26-30, 2006; CHED 492.

5. Liu, Y.; Bonvallet, P. A.; Vignon, S.; Khan, S. I.; Stoddart, J. F. Synthesis, characterization and stereochemistry of pretzelanes and a cyclic bis[2]catenane. Abstracts of Papers, 229th National Meeting of the American Chemical Society, San Diego, CA, Mar 13-17, 2005; ORGN 875.

4. Huang, T. J.; Liu, Y.; Brough, B.; Flood, A. H.; Bonvallet, P.; Tseng, H.-R.; Baller, M.; Magonov, S.; Stoddart, J. F.; Ho, C.-M. A Nano-Chemo-Mechanical Actuator Based on Artificial Molecular Machines. Proceedings of the 18th IEEE International Conference on Micro Electro Mechanical Systems, Miami, FL, Jan 30-Feb 3, 2005.

3. Flood, A. H.; Tseng, H.-R.; Liu, Y.; Wu, D.; Bonvallet, P. A.; Zhang, X.; Stoddart, J. F. Electrochemical switching of interlocked molecules in dynamic equilibrium. Abstracts of Papers, 227th National Meeting of the American Chemical Society, Anaheim, CA, Mar 28-Apr 1, 2004; ORGN 409.

2. Bonvallet, P. A.; Miller, K.;‡ Stoddart, J. F. Synthesis of a functionalized crown ether for attachment to a polymeric support. Abstracts of Papers, 227th National Meeting of the American Chemical Society, Anaheim, CA, March 28-April 1, 2004; CHED 1131.

1. Bonvallet, P. A.; Stoddart, J. F. Synthesis of redox switchable reverse recognition molecular muscles. Abstracts of Papers, 226th National Meeting of the American Chemical Society, New York, NY, Sept 7-11, 2003; ORGN 504.

‡ Undergraduate co-author

Further Reading

	Bibliographic Info	Call Number
	*Supramolecular Chemistry* Jonathan W. Steed, Jerry L. Atwood New York : Wiley, 2000	QD878 .S74 2000
	*Supramolecular Chemistry* Paul D. Beer, Philip A. Gale, David K. Smith New York : Oxford University Press, 1999	QD381 .B38 1999
	*Supramolecular Chemistry : Concepts and Perspectives* Jean-Marie Lehn Weinheim ; New York : VCH, c1995	QD381 .L43 1995

	*Organic Electronic Materials : Conjugated Polymers and Low Molecular Weight Organic Solids* R. Farchioni, G. Grosso (eds.) New York : Springer, 2001	QD382.C66 O74 2001

	General info on organic light-emitting diodes:
	oe Magazine
	Silicon Chip Magazine
	H.W. Sands Corp.
	Howstuffworks.com

	Vendor info on organic light-emitting diodes:
	Kodak NUVUE OLED Displays
	Philips Polymer OLED Photographs
	DuPont olight OLED Technology
	Cambridge Display Technology Polymer LED
	Universal Display Corporation OLED

IUPAC Compendium of Chemical Terminology