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Synthesis & Photochemistry of Longer Wavelength Azo Dyes

Project Full Title:

Increasing structural diversity of long-wavelength BF2-azo dye photoswitches to tune wavelength and add synthetic handles

Project Mentor(s):

Gillmore,Jason

Project Mentor(s) EMail:

gillmore@hope.edu

Project Start Date:

5/11/2020

Project End Date:

7/17/2020

Project Description:

My group of 3-4 undergraduates will focus on the synthesis of organic photoswitches that are triggered by long-wavelength visible or near infrared (NIR) irradiation.[1] Eventual application of these dyes will include their incorporation into polymer networks with the goal of developing NIR responsive polymeric materials for use in photomechanical applications such as wireless "soft robotic" actuators, binary optical switches and positioners, or surfaces with morphing topologies, at wavelengths other device components do not absorb and which may be compatible with biomedical applications including transdermal irradiation. However our newly awarded ACS PRF grant will first fund our study of far more fundamental structure property relationships of these dyes. We have recently discovered how to functionalize these dyes in ways their initial discoverer did not, and shown that substitution on the quinoline ring has as big or bigger effect than on the phenyl ring they initially studied. Thus we will explore a range of electron donating and withdrawing (push-pull) substitituents at multiple positions on both rings to see how far into the NIR we can push these dyes, and to correlate structural and spectral changes to further our fundamental understanding. Additional work may focus on adding synthetic handles to incorporate the dyes into more complex structures, and on exploring the range of reaction conditions to which the dyes are stable.

Students applying to this project should have an interest in doing primarily organic chemistry research, and should have at a minimum completed Organic I Lecture and Lab (CHEM 221 & 255 at Hope, or the equivalent elsewhere). The selected students will have the opportunity to gain familiarity with organic synthesis and photochemistry. Students will do all the characterization of structure and spectral properties using NMR, UV-Vis, GC/MS and other techniques.

Students also interested in computational modeling can additionally contribute to target selection based on computed spectral properties, and should note their computational interests in their application or via email. (Don't apply to both this project and my computational project - just apply to one but express interest in both.) Students with more detailed spectroscopic / analytical / physical interests may in the future pursue more detailed photophysical studies of the dyes. But organic synthesis will be the group's primary thrust for at least the next 18-24 months.

This is envisioned as a ten week paid summer project planned to be conducted from 5/11 - 7/17/2020, but eight or nine week periods may be negotiable, as might starting as early as 5/4. Hope students on this project are encouraged (perhaps even expected) to begin during the spring semester (CHEM 490 for 0 or 1 credit, or by tying this research to a related CHEM 256B Organic Chemistry II Laboratory elective independent synthesis project.) Likewise there is a definite expectation for all Hope students to continue the work into the Fall semester as well, unless we reach a different understanding in advance.

This project is primarily intended for Hope College students. Applications from exceptional students from external institutions (particularly two-year college students considering transferring to Hope) may be considered if space and funding allow.

References:

[1] Y. Yang, R.P. Hughes, I. Aprahamian, Near-Infrared Light Activated Azo-BF2 Switches, J. Am. Chem. Soc. 2014, 136, 13190.

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