Off-campus UMass Amherst users: To download campus access dissertations, please use the following link to log into our proxy server with your UMass Amherst user name and password.

Non-UMass Amherst users: Please talk to your librarian about requesting this dissertation through interlibrary loan.

Dissertations that have an embargo placed on them will not be available to anyone until the embargo expires.

Author ORCID Identifier



Open Access Dissertation

Document Type


Degree Name

Doctor of Philosophy (PhD)

Degree Program


Year Degree Awarded


Month Degree Awarded


First Advisor

Sankaran Thayumanavan

Subject Categories

Amino Acids, Peptides, and Proteins | Biochemistry | Chemical Actions and Uses | Chemistry | Heterocyclic Compounds | Investigative Techniques | Laboratory and Basic Science Research | Macromolecular Substances | Materials Chemistry | Medicinal and Pharmaceutical Chemistry | Medicinal Chemistry and Pharmaceutics | Medicinal-Pharmaceutical Chemistry | Nanotechnology | Organic Chemicals | Organic Chemistry | Pharmaceutics and Drug Design | Polymer Chemistry


Proteins have the capacity to bind specific sets of compounds known as ligands, these are small molecules with a recurrent theme in their molecular design that is a characteristic exploited here to (i) identify particular affinities of small molecules for proteins with the aim of using them as ligands, inhibitors, or targeting moieties in more complex systems by means of a methodology that screens small molecules based on protein affinity; (ii) decorate a self-assembling supramolecular system at different positions, making it responsive to a complementary protein with the aim of exploring differences in disassembly and sensitivity of the release of encapsulated guest molecules, depending on the initial location of the ligand upon binding to a specific protein; (iii) decorate self-assembling and crosslinkable dendrons aiming to introduce a system incorporating multiple ligands, sequentially responsive to a reducing environment, and to specific proteins.