Stoddart Mechanostereochemistry Group





Stoddart Mechanostereochemistry Group



Douglas C. Friedman

Graduate Student

Hometown: Encinitas, CA (USA)

Joined group: 2006

Left group: 2011


PhD – Chemistry – Northwestern University (2010)
MS – Chemistry – University of California, Los Angeles (2008)
BS – Chemical Biology – University of California, Berkeley (2006)


Stoll, R.S.; Friedman, D.C.; Stoddart, J.F. Mechanically Interlocked Mechanophores by Living-Radical Polymerization from Rotaxane Initiators. 2011, Submitted for Publication.

Coskun, A.; Spruell, J.M.; Barin, G.; Fahrenbach A.C.; Forgan, R.S.; Colvin, M.T.; Carmielli, R.; Benítez, D.; Tkatchouk, E.; Friedman, D.C.; Sarjeant, A.A.; Wasielewski, M.R.; Goddard, W.A.; Stoddart, J.F. Mechanically Stabilized Tetrathiafulvalene Radical Dimers. J. Am. Chem. Soc. 2011, 133, 4538–4537. LINK

Basu, S.; Coskun, D.C.; Friedman, D.C.; Olson, M.A.; Benitez, D.; Tkatchouk, E.; Stoddart, J.F. Donor Acceptor Oligorotaxanes Made to Order. Chem. Eur. J. 2011, 17, 2107–2119. LINK

Barin, G.; Coskun, A.; Friedman, D.C.; Olson, M.A.; Colvin, M.T.; Camielli, R.; Dey, S.K.; Bozdemir, O.A.; Wasielewski, M.R.; Stoddart, J.F., A Multistate Switchable [3]Rotacatenane. Chem. Eur. J. 2010, 17, 213–222. LINK

Spruell, J.M.; Coskun, A.; Friedman, D.C.; Forgan, R.S.; Sarjeant, A.A.; Trabolsi, A.; Fahrenbach, A.C.; Barin, G.; Paxton, W.F.; Dey, S.K., Olson, M.A.; Benitez, D.; Tkatchouk, E.; Colvin, M.T.; Carmielli, R.; Caldwell, S.T.; Rosair, G.M.; Hewage, S.G.; Declairoir, F; Seymour, J.L.; Slawin, A.M.Z.; Goddard, W.A.; Wasielewski, M.R.; Cooke, G.; Stoddart, J.F. Highly stable TTF radical dimers in [3]catenanes. Nature Chem. 2010, 2, 870–879. LINK

Forgan, R.S.; Friedman, D.C.; Stern, C.L.; Bruns, C.J.; Stoddart, J.F. Directed self-assembly of a ring-in-ring complex. Chem. Commun. 2010, 46, 5861–5863. LINK

Trabolsi, A.; Fahrenbach, A.C.; Dey, S.K.; Share, I.A.; Friedman, D.C.; Basu, S.; Gasa, T.B.; Khashab, N.M.; Saha, S.; Aprahamian, I.; Khatib, H.A.; Flood, A.H.; Stoddart, J.F. A tristable [2]pseudo[2]rotaxane. Chem. Commun. 2010, 46, 871–873. LINK

Trabolsi, A.; Khashab, N.M.; Fahrenbach, A.C.; Friedman, D.C.; Colvin, M.T.; Coti, K.; Benitez, D.; Tkatchouk, E.; Olsen, J.-C.; Belowich, M.E.; Carmielli, R.; Khatib, H.A.; Goddard, W.A.; Wasielewski, M.R.; Stoddart, J.F. Radically Enhanced Molecular Recognition. Nature Chem. 2010, 2, 42–49. LINK

Khashab, N.M.; Belowich, M.E.; Trabolsi, A.; Friedman, D.C.; Valente, C.; Lau, Y.; Khatib, H.A.; Zink, J.I.; Stoddart, J.F. pH-Responsive Mechanised Nanoparticles Gated by Semirotaxanes. Chem. Commun. 2009, 5371–5373. LINK

Spruell, J.M.; Paxton, W.F.; Olsen, J-C.; Benitez, D.; Tkatchouk, E.; Stern, C.L.; Trabolsi, A.; Friedman, D.C.; Goddard, W.A.; Stoddart, J.F. A Push-Button Molecular Switch. J. Am. Chem. Soc. 2009, 11571–11580. LINK

Khashab, N.M.; Trabolsi, A.; Lau, Y.; Ambrogio, M.W.; Friedman, D.C.; Khatib, H.A.; Zink, J.I.; Stoddart, J.F. Redox- and pH-Controlled Mechanized Nanoparticles. Eur. J. Org. Chem. 2009, 1669–1673. LINK
*Special issue in Honor of Alain Krief

Coskun, A.; Friedman, D.C.; Li, H.; Patel, K.; Khatib, H.A.; Stoddart, J.F. A Light-Gated STOP-GO Molecular Shuttle. J. Am. Chem. Soc. 2009, 131, 2493–2495. LINK

Trabolsi, A.; Hmadeh, M.; Khashab, N.M.; Friedman, D.C.; Belowich, M.E.; Humbert, N.; Elhabiri, M.; Khatib, H.A.; Albrech-Gary, A.-M.; Stoddart, J.F. Redox-Driven Switching in Pseudorotaxanes. New J. Chem. 2009, 22, 254–263. LINK
*Special issue in Honor of Jean-Pierre Sauvage
**Front Cover

Click here to see all DCF publications in the Stoddart Lab


Born and raised in a sunny beach town in Southern California, I found myself traveling extensively all the way to the Bay Area to study organic chemistry at the University of California, Berkeley. It was a long and grueling experience filled with many sleepless nights, too many shots of espresso, and the occasional trip to Lake Tahoe. Aside from the usual undergraduate frolicking and dilly-dallying, I managed to dabble in palladium π-allyl chemistry for in vitro, site-selective protein modification under the guidance of Prof. Matt Francis.

I then migrated to UCLA and found myself wondering about the world of materials and the future of nanoscience. Strangely enough, I find myself having moved 2000 miles to the state of Illinois, the Land of Lincoln (or should I say Obama). I am currently studying the dynamics and stereochemistry of interlocked molecules by NMR spectroscopy. Hopefully any conclusions I may reach in the future will bring me fame, fortune, and much to leave to posterity.

When I’m not in lab, I spend my remaining one or two hours a week enjoying soccer, sailing, scuba diving, snowboarding, other activities starting with “s,” and perusing the latest products released by Apple. I love traveling to other countries, including England, Scotland, Czech Republic, Israel, Australia, and Mexico (“I grew up 40 miles from the border”); hopefully I’ll be seeing most of Western Europe sometime soon. Most of my domestic diversions revolve around friends, family, and my fish, Fish.


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