College
Buchtel College of Arts and Sciences
Date of Last Revision
2025-05-06 06:38:30
Major
Biochemistry
Honors Course
CHEM 497
Number of Credits
2
Degree Name
Bachelor of Science
Date of Expected Graduation
Spring 2025
Abstract
Chalcones are a class of naturally occurring compounds found in plants, which have a general structure of Ar–CO–CH=CH–Ar’. They have shown significant potential as tunable organic fluorophores due to their extended π-conjugation and structural simplicity. In this study, a 2-hydroxy-substituted chalcone featuring a terminal dimethylamino group was synthesized via a pyrrolidine-catalyzed aldol condensation and characterized for its photophysical properties. The electron-donating and -accepting ends of the molecule establish an intramolecular charge transfer (ICT) pathway, while the hydroxyl group enables excited state intramolecular proton transfer (ESIPT), leading to complex emission behavior. Room temperature fluorescence analysis revealed broad, featureless emission, while low-temperature studies unveiled a well resolved vibronic structure consistent with distinct tautomeric states. Selective excitation at specific wave lengths could give two different emission bands, attributable to either enol or keto forms. The observation highlighted the role of excited-state proton dynamics and molecular geometry in modulating fluorescence. These findings suggest that this chalcone derivative serves as a valuable model compound for exploring vibronic coupling, ICT, and ESIPT processes in small-molecule organic fluorophores.
Research Sponsor
Yi Pang
First Reader
David Modarelli
Second Reader
Yilin Liu
Honors Faculty Advisor
Yi Pang
Proprietary and/or Confidential Information
No
Recommended Citation
Hilliker, Margaret, "Synthesis of Noval Hydroxy Chalcone and Study of Fluorescent Properties" (2025). Williams Honors College, Honors Research Projects. 2012.
https://ideaexchange.uakron.edu/honors_research_projects/2012