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Organic Photochemistry with the Harbron Group

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Page 1: Organic Photochemistry - College of William & Mary · 2020-06-13 · Organic Photochemistry Author: Harbron, Elizabeth J Created Date: 9/20/2017 9:08:30 AM

Organic Photochemistry

with the

Harbron Group

Page 2: Organic Photochemistry - College of William & Mary · 2020-06-13 · Organic Photochemistry Author: Harbron, Elizabeth J Created Date: 9/20/2017 9:08:30 AM

Photochemists use light…

• to do chemistry

• to interrogate molecules

• or to do both

AlUV B

pre-irrad.

post-UV irrad.

post-VIS irrad.

Page 3: Organic Photochemistry - College of William & Mary · 2020-06-13 · Organic Photochemistry Author: Harbron, Elizabeth J Created Date: 9/20/2017 9:08:30 AM

Our Focus

• Stimulus-responsive fluorescence

FL+ stimulus

- stimulus

FL

FL FL

FL FL

Page 4: Organic Photochemistry - College of William & Mary · 2020-06-13 · Organic Photochemistry Author: Harbron, Elizabeth J Created Date: 9/20/2017 9:08:30 AM

Fluorescence properties make it particularly

well-suited to sensing and imaging

• sensitivity

• many observables

– intensity

– wavelength (color)

– lifetime

– anisotropy

• spatiotemporal resolution

Page 5: Organic Photochemistry - College of William & Mary · 2020-06-13 · Organic Photochemistry Author: Harbron, Elizabeth J Created Date: 9/20/2017 9:08:30 AM

Current Project Areas

• Light

– fluorescence intensity modulation

induced by visible light

– “release and report” system for

simultaneous photocontrol of analyte

and fluorescence detection

• Mercury

– mercury ion sensing in water with doped

conjugated polymer nanoparticles

• Green Fluorescent Protein

– new GFP-dye analyte sensors

Page 6: Organic Photochemistry - College of William & Mary · 2020-06-13 · Organic Photochemistry Author: Harbron, Elizabeth J Created Date: 9/20/2017 9:08:30 AM

Conjugated Polymer Nanoparticles

• CPNs (Pdots) can be used as the fluorophore in

stimulus-responsive fluorophore-dye constructs

– Stably suspended in water

– Covalent or non-covalent dye incorporation

– Photophysical advantages

+stimulus

FRET

Page 7: Organic Photochemistry - College of William & Mary · 2020-06-13 · Organic Photochemistry Author: Harbron, Elizabeth J Created Date: 9/20/2017 9:08:30 AM

Fluorescence Photomodulation with lvis

• Goal: off-to-on photoswitching with visible light

• Application: super-resolution microscopy (2014 Nobel Prize)

Page 8: Organic Photochemistry - College of William & Mary · 2020-06-13 · Organic Photochemistry Author: Harbron, Elizabeth J Created Date: 9/20/2017 9:08:30 AM

Photorelease & Report

• Goal: achieve photocontrol of analyte with simultaneous

fluorescence readout

• Application: biological imaging experiments

Page 9: Organic Photochemistry - College of William & Mary · 2020-06-13 · Organic Photochemistry Author: Harbron, Elizabeth J Created Date: 9/20/2017 9:08:30 AM

Mercury Detection

• Goal: sensitive, selective, ratiometric detection of

mercury ions in water

• Application: environmental testing, imaging

Hg2+

FRET

- HgS

-Hg

CPNs fluoresce

RB-SL “silent”

+Hg

Hg promotes RB-Sl RB-Hg

CPNRB-Hg FRET activated

CPN and RB-Hg fluoresce

Page 10: Organic Photochemistry - College of William & Mary · 2020-06-13 · Organic Photochemistry Author: Harbron, Elizabeth J Created Date: 9/20/2017 9:08:30 AM

GFP-based Sensors

• Goal: develop new fluorescent sensors based on GFP-

dye conjugates

• Application: biological imaging

image credit: Zeiss Microscopy Online Campus at FSU National

High Field Magnet Lab

Page 11: Organic Photochemistry - College of William & Mary · 2020-06-13 · Organic Photochemistry Author: Harbron, Elizabeth J Created Date: 9/20/2017 9:08:30 AM

Harbron Research Lab

+ ?

Matt McCarron MS ‘18, Lisa Graves MS ’19, Tyler

Larson ‘18, Hank Hannon ‘19, Andrew Dahik ‘19,

Elizabeth Amato ‘18

You?

Page 12: Organic Photochemistry - College of William & Mary · 2020-06-13 · Organic Photochemistry Author: Harbron, Elizabeth J Created Date: 9/20/2017 9:08:30 AM

Lab Life

Measuring

Communicating

Making

Fun

Page 13: Organic Photochemistry - College of William & Mary · 2020-06-13 · Organic Photochemistry Author: Harbron, Elizabeth J Created Date: 9/20/2017 9:08:30 AM

Making

• Organic synthesis

• Purification (chromatography)

• Characterization (NMR)

• Nanoparticle preparation

Page 14: Organic Photochemistry - College of William & Mary · 2020-06-13 · Organic Photochemistry Author: Harbron, Elizabeth J Created Date: 9/20/2017 9:08:30 AM

Measuring

• Absorption and fluorescence

• Response to stimulus (we have lights! lasers!)

Page 15: Organic Photochemistry - College of William & Mary · 2020-06-13 · Organic Photochemistry Author: Harbron, Elizabeth J Created Date: 9/20/2017 9:08:30 AM

Communicating

• Group meeting

• Undergraduate research symposium

Page 16: Organic Photochemistry - College of William & Mary · 2020-06-13 · Organic Photochemistry Author: Harbron, Elizabeth J Created Date: 9/20/2017 9:08:30 AM

#labhood