Submission Date

7-26-2024

Document Type

Paper- Restricted to Campus Access

Department

Chemistry

Faculty Mentor

Ryan R. Walvoord

Comments

Presented during the 26th Annual Summer Fellows Symposium, July 19, 2024 at Ursinus College.

This research was supported by the Organic Syntheses 2024-2025 Research Grant for Faculty at Principally Undergraduate Institutions.

Project Description

Fluorescence imaging is a tool often used in biology and for the detection of analytes of interest. However, many chemical tools used have limitations, such as difficult functionalization, poor solubility, and undesirable photophysical properties. As a result, there is a need for improved chemical tools for fluorescence imaging and detection purposes that can be used in a wider range of contexts without these limitations. Rhodols, a hybrid of fluorescein and rhodamine, have a number of advantages over their predecessors, including increased photostability and decreased pH-sensitive fluorescence. However, rhodols are traditionally difficult to synthesize due to lengthy syntheses often incompatible with different functional groups and expensive materials. Few rhodols are commercially available, generally costing significantly more than their fluorescein counterpart. This project explores a more efficient synthesis of rhodols, allowing for greater functional group tolerance and using more widely-available reagents in mild conditions. The rhodols experience a bathochromic shift with increasing solvent polarity as well as generally pH-independent fluorescence. These properties could allow rhodols to be used in imaging without regard for environmental pH, as well as the functional group tolerance allowing for different substituents to label specific analytes.

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