Survival of the Fittest! Chemistry Boot Camp at MIT

Have you been stressed by your chemistry lab experience? You're not alone - every January, groups of freshmen at MIT take a class called 5.301 Chemistry Lab Techniques, also known as "Chemistry Boot Camp". Noted for its intensity and very short period (4 weeks), students learn techniques and equipment that are commonly used in a chemistry research lab - NMR, organic synthesis, crystallization, gravity filtration, rotovap, thin-layer and column chromatography. In the process of learning, they spill chemicals, break glassware, generate toxic gases, and share some of their anxieties of meeting the challenges this course entails. During the course, each student has a transformative moment that helps them decide if they are meant for research.

The videos document the journey of these freshmen from nervous newbie to savvy lab assistant, all of whom survive the ordeal and emerge with newfound love for research and chemistry.

Being in chemistry lab is a human experience. There is laughter, crying, and cursing. But in the end, there is bonding and friendship from sharing a sometimes difficult experience together.

Episodes of Chemistry Boot Camp at MIT

Same or Different? How a Simple Carbon Atom Leads to Complex Natural Compounds

A deceptively simple atom like carbon exhibits diverse styles of bonding that can lead to a plethora of complex organic molecules:

Carbon's flexibility in bonding makes it possible for molecules to have structural complexity, such as nonsuperimposable mirror images known as enantiomers:

In this example, these are not the same molecule even though the way the individual atoms are connected is the same. Because the 3-dimensional spatial arrangement around the central carbon atom is different, these are also known as chiral molecules or enantiomers, and carbon is called a chiral center.

There is a nice video created by Lydia Flynn where she demonstrates how molecules can be chiral using molecular models.

Chirality/Basic Concept Explained

Chiral molecules can be found in nature, and sometimes we need an extra few seconds to check if we are seeing the same molecule or two different molecules. One example is a compound produced female gypsy moths known as disparlure. It turns out that only one form of this molecule (in purple) is attractive to male moths.

 

Female Gypsy Moth

"Lymantria dispar 8-8-2006 19-20-14" by Opuntia. 

Licensed under CC BY-SA 3.0 via Wikimedia Commons

Molecular models show these are enantiomers and not the same molecule of disparlure.

Brown tube sponge from the National Museum of Natural History (image by Rachel Cooper)

Sceptrin is a compound made by the brown tube sponge. It is currently researched for its antibiotic potential.

 

These are enantiomers of sceptrin, a compound whose structure was first synthesized in 2004 by scientists in The Scripps Research Institute.

Molecular models again illustrate the nonsuperimposability of these mirror image isomers.

The Most Astounding Fact-by Neil deGrasse Tyson

He was asked by a Time reader, "What is the most astounding fact you can share about the universe?" This beautifully edited video by Max Schlickenmeyer highlights Dr. Tyson's answer. Essentially the chemistry that created the atoms and elements of the universe is the same chemistry made us. That is how we are connected to the universe.

His eloquent response is here.

Image credit: NASA/CXC/SAO: X-ray; NASA/JPL-Caltech: Infrared

Inspiration from Worms and Mussels - A Sutureless Way to Do Surgery

Healing from surgery can be complicated by using sutures in particular parts of our bodies. Depending on the type of material (silk or polymer-based), the immune system can have a reaction, prolonging healing times to as long as 4 months! 

So what is a possible alternative that can be easily applied to sensitive tissue and maintain structural integrity long enough for healing? One clever organism that bioengineers are currently studying is the sandcastle worm or Phragmatopoma californica.


 

By Fred Hayes for the University of Utah [CC BY-SA 3.0 (http://creativecommons.org/licenses/by-sa/3.0)], via Wikimedia Commons

Scott Creek, Santa Cruz Co., CA; 17 Mar 2008

Sandworms are typically shy creatures, coming out only to catch microorganisms and grain particles. Their tubules can be found along Baja California and Mexico.

Professor of Bioengineering Russell Stewart from the University of California Santa Barbara is currently studying waterproof adhesives that sandcastle worms (and caddisflies) use to create their elaborate constructions. In his research, he has determined that the forces of attraction are electrostatic (oppositely charged ions attracting each other) with some cross-linking between catechol and DOPA polymers.

Inspired by the worm's ability to create an adhesive that works in water, medical doctor Nora Lang and bioengineers Maria Pereira and Jeffrey Karp at Harvard Medical School teamed up with other scientists to create an adhesive that works in vivo in repairing tiny defects in sensitive tissue.

 Exposure of hydrophobic light-activated adhesive polymer (HLAA) to UV light creates crosslinking

(image from http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4157752/)

Using a polymer of glycerol and sebacic acid, they exposed the molecules to UV light and created crosslinks. This resulted in a highly flexible material that could be gently applied to very small tears in a carotid artery:

In this carotid artery, a hole was created and then sealed with HLAA polymer. After 24 hours, the seal remained intact. 

(from http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4157752/)

With its recently tested potential, light-activated liquid polymers may have a place on the surgeon's tray in place of sutures.

Articles and Resources of Interest:

*A Blood-Resistant Surgical Glue for Minimally Invasive Repair of Vessels and Heart Defects; by N. Lang, M.J. Pereira, Y. Lee, I. Friehs, N.V. Vasilyev, E.N. Feins, K. Ablasser, E.D. O'Cearbhaill, C. Xu, A. Fabozzo, R. Padera, S. Wasserman, F. Freudenthal, L.S. Ferreira, R. Langer, J.M. Karp, and P.J. del Nido

*Letting Bio-Inspired Solutions Evolve : Q &A with Jeff Karp

Amazing Uses of Bubble Wrap

The next time you toss that bubble wrap from your next package, think of the possible applications for it. What else can you do with air bubbles encased in plastic?

Interestingly, when it was created in 1957 by engineers Alfred Fielding and Marc Chavannes, the original plan was to cover walls with a 3-dimensional textured pattern:

Image from Mental Floss, bubble wrap was considered a distinctive wall covering.

Only three years later it was discovered to be a superb packing material. Bubble wrap itself is made of low-density polyethylene (LDPE), a polymer of ethylene monomers that has some branching.

"Bubble Wrap" by User Consequencefree on en.wikipedia. Licensed under CC BY-SA 3.0 via Wikipedia Commons

Branching around polyethylene reduces strands of it to pack closely, and this decreases its density.

Images from http://faculty.uscupstate.edu/llever/Polymer%20Resources/Topology.htm by David Whisnant

More recently,  other amazing uses for bubble wrap have emerged. One example is from Bradley Hart, an artist in New York who injects different colors of paint into the bubbles to create portraits and landscapes:

Image from http://www.visualnews.com/test/2013/03/paintings-made-by-injecting-paint-in-bubble-wrap/

Is there a place for bubble wrap in a chemistry lab? Most definitely! Professor George Whitesides and colleagues from Harvard University came up with some clever applications. Because the material is so cheap (about 60 cents per square meter) and the same area can have up to 5000 bubbles, the team discovered that the bubbles can safely hold liquid samples. This lead to a number of experiments testing the reliability of these plastic bubble holders:

Bubbles of Allura Red and rhodamine B dye - a test to see if liquid reagents can be stored and tested for absorbance measurements.

Image from dx.doi.org/10.1021/ac501206m; Anal. Chem. 2014, 86, 7478-7485.

Samples of E. coli grown in yeast and tryptone medium. Bubbles can be used to grow colonies of bacteria and microorganisms.

Image from dx.doi.org/10.1021/ac501206m; Anal. Chem. 2014, 86, 7478-7485.

A bubble can act as an electrochemical cell! Here 2 carbon electrodes are used to measure the current from different concentrations of ferrocyanide.

According to Professor Whitesides, bubble wrap can be repurposed to carry out a few chemistry and biology experiments in labs that normally cannot afford conventional test tubes and petri dishes.

Can you think of other unusual applications for bubble wrap? Test it out!

For further reading:

Adaptive Use of Bubble Wrap for Storing Liquid Samples and Performing Analytical Assays; David K. Bwambok, Dionysios C. Christodouleas, Stephen A. Morin, Heiko Lange, Scott T. Phillips, and George M. Whitesides; dx.doi.ord/10.1021/ac501206m; Anal. Chem. 2014, 86, 7478-7485.

The Power of Transesterification - Making Biodiesel and Turning an Organic Network into Glass

You may not have heard of transesterification but probably heard about the compound this reaction produces: biodiesel. As a general reaction, it involves taking an ester and an alcohol and changing them into a different ester and alcohol.

You can think of this as transforming one ester into another. In the synthesis of biodiesel, transesterification typically starts with a fat which is a triester molecule. After reacting with methanol and a catalyst, a high yield of methyl esters or biodiesel can be collected.

 

Image from Dogpatch Biofuels

A few years ago this reaction was discovered to be highly useful in taking an organic polymeric network and turning it into a resin that has the hardness of glass, the ability to be reshaped, and is recyclable. Researchers Damien Montarnal, Mathieu Capelot, François Tournilhac, and Ludwik Leibler from Laboratoire Matiere Molle et Chimie in Paris, France modified bisphenol A diglycidyl ether with some di- and tricarboxylic acids to create an organic polymeric network with ester and alcohol functional groups.

 

Credit: Cyril Fresillon/CNRS

The stoichiometry and reversibility of this reaction allow the number of ester and alcohol groups to remain the same. The flexibility in changing how cross-links are formed enables this material to adopt various complex shapes.

For further reading, check out:

*A Plastic that Behaves Like Glass by Bethany Halford

*New revolutionary material can be worked like glass (press release)

*Silica-Like Malleable Materials from Permanent Organic Networks by Damien Montarnal, Mathieu Capelot, François Tournilhac, and Ludwik Leibler; Science 18 November 2011: Vol. 334 no. 6058 pp. 965-968; DOI: 10.1126/science.1212648

 

Chemistry in a Work of Art - Light Spectra by Bev Precious

Light Spectra by Bev Precious, an aluminum and dichroic glass sculpture in the foyer of the chemistry building at UW-Madison (photo by Jeff Miller)

The first thing a visitor might see upon entering the foyer of the chemistry building at UW-Madison is a brilliant aluminum and dichroic glass sculpture suspended overhead. "Light Spectra" was created in 2001 by American sculpture Bev Precious who used the interplay of metal and dichroic glass to create an eye-catching work of art.

The creation of dichroic glass involves a process called electron beam physical vapor deposition, where 10,000 V of electricity are concentrated in an electron beam and vaporizes a mixture of quartz and metal oxides of titanium, chromium, aluminum, zirconium, or magnesium. This mixture vapor is eventually deposited onto a glass surface and can be applied a layer at a time. Layer thicknesses are precisely controlled to allow multiple colors to be produced on the same glass.

Image from Center for Nanoscale Science and Engineering

Here is a cool video, produced by a company called Coatings By Sandberg, showing how dichroic glass is made.

Geodesic pattern glass from CBS

Dichroic glass has the special property of transmitting light of one color and reflecting light in a different color. Hence as you walk around a dichroic sculpture, you would see different colors evolve at different angles of observation.