S. "Thai" Thayumanavan

Associate Professor of Chemistry, University of Massachusetts

Email: thail@chem.umass.edu
S. Thayumanavan's Chemistry Web Site

Ph.D.: University of Illinois
Postdoctoral training: Caltech

Design and synthesis of biomimetic organic molecules and polymers and applications of custom-designed molecules in biology and material science.

Research in our group is focused on the design and synthesis of novel macromolecules (dendrimers and polymers) that have applications in chemistry, biology and material science. Examples of these applications include catalysis, drug design & delivery, and light emitting, light harvesting & sensory materials. The tools we use for tackling these projects involve design, synthesis and characterization of small organic molecules and macromolecules of various dimensions.

From a broad perspective, our research at UMass involves mainly two areas: (i) design and synthesis of new macromolecules that adapt different conformations upon change in the external environment; (ii) discovery of novel molecular-scale electronic and photonic materials by a molecular engineering approach. Students working in the group use synthetic organic and synthetic polymer chemistry along with physical organic characterization techniques to address issues in chemistry and at the interface of chemistry with other sciences, in particular with biology and materials. The students in the group thus gain expertise in organic synthesis, polymer synthesis, characterization techniques used for small molecules and polymers, and molecular design strategies to address complex problems at the interface of the sciences.

Biological macromolecules (proteins) have the ability to adapt unique secondary structures upon small changes in their environment. It is extremely interesting to mimic this fundamental molecular recognition process with custom designed macromolecules. Efforts are underway towards this long-term goal in the group. The resultant materials could also be developed to function as smart materials in sensors and drug delivery applications. Projects have also been designed toward these application-oriented goals.

Engineering molecules to obtain molecular-scale (nanoscale) electronic and photonic device is an exciting area of research, since these molecules hold the promise of reducing the feature sizes of these devices. Our group is particularly interested in developing new molecular architectures for light harvesting materials (solar energy harvest and storage). With both biological and materials applications, the properties of the custom designed molecules will be investigated both in-house and collaboratively

Representative publications:

Bronk, K.; Thayumanavan, S. " Synthesis of Non-conjugated Dendrons with a Redox Gradient " J. Org. Chem. 2003, 68, 5559-5567.

Thayumanavan, S.; Bharathi, P.; Sivanandan, K.; Vutukuri, D.R. “Dendrimers as Biomimetic Macromolecules” Comptes Rendus Chimie, in press (invited review).

Vutukuri, D.; Sivanandan, K.; Thayumanavan, S. " Synthesis of dendrimers with multifunctional periphery using an ABB' monomer" Chem. Commun.2003, 796-797.

Vutukuri, D.; Bharathi, P.; Yu, Z.; Rajasekaran, K.; Tran, M.-H.; Thayumanavan, S. "A Mild Deprotection Strategy for Allyl Ether and Alloc- Protecting Groups: Implications in Sequence Specific Dendrimer Synthesis" J. Org. Chem. 2003, 68, 1146-1149.

Sivanandan, K.; Vutukuri, D.; Thayumanavan, S. "Functional Group Diversity in Dendrimers" Org. Lett. 2002, 4, 3751-3753.

Ganesh, R.N.; Shraberg, J.; Sheridan, P.G.; Thayumanavan, S. "Synthesis of Difunctionalized Dendrimers: An Approach to Main Chain Poly(dendrimers)" Tetrahedron Lett. 2002, 43, 7217-7220.

Basu, A.; Thayumanavan, S. “Configurational Stability and Stereoinformation Transfer in the Reactions of Enantioenriched Organolithium Intermediates” Angew. Chem., Int. Ed. 2002, 41, 716-738.

Bharathi, P.; Zhao, H.; Thayumanavan, S. “Toward Globular Macromolecules with Functionalized Interiors: Design and Synthesis of Dendrons with an Interesting Twist” Org. Lett. 2001, 3, 1961-1964.

Bronk, K.; Thayumanavan, S. “Design and Synthesis of Non-Conjugated Monodendrons with Triarylamine Repeating Units” Org. Lett. 2001, 3, 2057-2060.

Zhao, H.; Tanjutco, C.; Thayumanavan, S. “Design and Synthesis of Stable Triarylamines for Hole-Transport Applications” Tetrahedron Lett. 2001, 42, 4421-4424.