UNIVERSITY OF MASSACHUSETTS BOSTON GREEN CHEMISTRY NEWSLETTER Issue 2 December 2014 The Green Chemistry Track in the Chemistry Ph.D. Program at UMass Boston was established in 2002. It is the first such program in the world. Students obtaining a degree from this program will be prepared for conventional chemistry jobs in industry, government and academia. Green chemistry involves an ecologically sustainable view of chemical research, development, and manufacture. Toxicological understanding and environmental fate are necessary components to understanding the entire "molecular life cycle" of any commercial endeavor. The unique complement of the chemistry and biology department as well as the school for the environment faculty has allowed the University of Massachusetts Boston to create such a program. http://www.umb.edu/greenchemistry News UMass Boston’s ACS Student Chapter has earned the Green Chemistry Chapter Award for the second year in a row. Dr. Berkeley Cue and Prof. Wei Zhang are serving on the international advisory board of 2015 Drug Discovery & Therapy World Congress in Boston. Graduate student Shuai Liu (Prof. Wei Zhang’s lab) is the recipient of green chemistry graduate scholarship designated by Dr. John Warner as part of his 2014 SCI Perkin Medal Award. Graduate student Courtney Ngai (Dr. Hannah Sevian’s lab) received a travel scholarship from NSF and attended and presented a poster “Chemical Identity: What is this substance?” at the Gordon Research Conference on Green Chemistry in Hong Kong in August. John Collins (Prof. Foster’s lab) defended his sustainable energyrelated Ph.D. thesis “Tuning Carbon Microstructure for Advancing Electrochemical Energy Storage” in June. Graduate student Maria Kipreos (Dr. Michelle Foster’s lab) received the travel award and attended the ACS Summer School on Green Chemistry & Sustainable Energy at the Colorado School of Mines in Golden, Colorado in July. Korea Science Academy of Kaist (KSA) sent a group of high school students to Boston for science workshops at MIT, Tufts University, Boston University, and UMass Boston. Prof. Wei Zhang was invited to give seminars on the topic of green chemistry in October. Prof. Wei Zhang is invited to give a talk “Recyclable Organocatalysis for Asymmetric Fluorination” at the 2nd Annual Symposium and Workshop of the Global Green Chemistry Centres in Cape Town, South Africa in August. Prof. Wei Zhang is invited to give a talk “Recent Development on Green Solvents for Industrial Applications” at ASC Sustainability Forum - A Supply Chain Discussion of Trends and Market Drivers in Baltimore In July. Prof. Wei Zhang is invited to give a talk “Fluorous Technologies for Green Organic Synthesis and Catalysis” at the Next Steps in Green Chemistry Research Workshop organized by Green Chemistry Initiative at the University of Toronto in May. Recent Publications Maertens, A.; Anastas, N.; Spencer, P. J.; Stephens, M.; Goldberg, A.; Hartung, T. “Food for Thought - Green Toxicology” ALTEX 2014, 31, 243-249. Cho, H.; Török, F.; Török, B. “Energy efficiency of heterogeneous catalytic microwave-assisted organic reactions” Green Chem. 2014, 16, 3623-3634. Thuo, M. M.; Martinez, R. V.; Liu, X.; Atkinson, M. B.; J. Bloch, J. F. Whitesides, G. M. “Low-Cost microfluidic devices derived from embossed hydrophobic paper” Chem. Mater. 2014, 26, 4230-4237. Solan, A.; Nisanci, B.; Belcher, M.; Young, J.; Schäfer, C.; Wheeler, K. A.; Török, B.; Dembinski, R. “Catalyst-free chemo-/regio-/stereo-selective amination of alk-3-ynones. Synthesis of 1,5-benzodiazepines and 3-amino-2-alkenones.” Green Chem., 2014, 16, 1120-1124 McKeown, M.; Shaw, D.; Fu, H.; Liu, S.; Xu, X.; Marineau, J.; Huang, Y.; Zhang, X.; Buckley, D.; Lin, C.; Kadam, A.; Zhang, Z.; Blacklow, S.; Qi, J.; Zhang, W.; Bradner, J. “Biased multicomponent reactions to develop novel bromodomain inhibitors” J. Med. Chem. 2014, 57, 9019-9027. UMB GreenChemistry 1 People in Green Chemistry Shuai Liu Each year the Society of Chemical Industry awards one scientist in the United States as the recipient of the Perkin Medal Award for notable work in applied chemistry. In 2014 the Perkin Medal Award was given to Dr. John C. Warner (above middle), one of the world’s leading advocates of green chemistry. Each recipient of this award then gets to choose an exceptional student to receive the Perkin Scholarship, an amount of $5000, for their excellence in applied chemistry and contributions to research. This year, the recipient of this scholarship was UMass Boston’s Shuai Liu! In 2012 Shuai (above right) received his bachelor’s degree in chemistry at Lanzhou University in China, far from his hometown in Huaiyang County. Shuai is a 3rd year Ph.D. student working with Dr. Wei Zhang at UMass Boston on applications of green chemistry principles for drug discovery. Currently Shuai is working on a collaboration project with Harvard Medical School and Dana Farber Cancer Institute developing benign synthetic methods for the preparation of compounds which may be invaluable to the medical field. In order to receive this scholarship Shuai and his girlfriend, He Huang, (above left) traveled to Philadelphia to attend a special award ceremony and banquet. Shuai is appreciative to have been able to share this achievement in the company of He, especially since his family is in China. Although not with them every day, he knows that chasing his dreams would not be possible without their encouragement and support. Become a Green Chemist Undergraduate Opportunity Are you an undergraduate student of chemistry of biochemistry who is looking to get more involved on campus and network with colleagues and faculty? Enrich your academic career by becoming a member of UMass Boston American Chemical Society Student Chapter. For more information visit: http://www.umb.edu/academics/csm/chemis try/beyond_the_classroom/acs Graduate Opportunity If you are interested in an innovative and exciting career in science, then the Green Chemistry Track in the Chemistry PhD program is a perfect opportunity for you. As the world moves to focus on sustainability in both an environmental and lab setting more job opportunities arise within industry, government and academia. For more information visit: http://www.umb.edu/academics/csm/ch emistry UMB GreenChemistry 2 Green Chemistry Principle #2 Atom Economy As chemists strive to produce less waste and create more efficient reactions, it becomes important that they have some way of measuring the efficiency so that a comparison can be made between processes to decide which is the more appropriate to use. Atom Economy is one of many green indicators designed to help chemists analyze reactions mathematically to see if they are efficient. Atom Economy has become known as the second Green Chemistry Principle and was introduced by Barry Trost in the early 1990’s. Other green indicators such as percent yield and E-factor are also helpful however; atom economy is the best one to use when comparing many processes. Atom Economy is a ratio of molecular weight of desired product and the molecular weight of the reactants in a reaction which is then multiplied by 100. A high Atom Economy indicates that most of the reactants get converted to the product, this is a desired result. On the other hand, a low atom economy tells the scientist that a large amount of reactants to dot get turned into products and therefore is not efficient and there may be a better alternative. One of the goals of green chemistry is to reduce waste and therefore have less to deal with in the end, therefore, if you can convert more of your reactant atoms to product atoms then you will yield less waste in the end. If you want to read more about this principle and how to apply it to your own work the following is a link to a great paper entitled, “Real atom economy and its application for evaluation the green degree of a process”. For more detailed information about this principle in the literature please visit: http://www.springerlink.com/index/T1VKM387 WJ10T8G0.pdf NESSE Network of Early-Career Sustainable Scientists and Engineers (NESSE) is an international and interdisciplinary network of early-career scientists that share a common vision: a sustainable future for all. The mission of NESSE is to provide a platform for scientists to inspire and encourage each other toward sustainable innovation, building a new generation of researchers who are driven by green practices. NESSE also aims to educate the public, enable collaboration and mentoring between scientists and engineers, and encourage leadership and advocacy in the scientific community. Participation in NESSE ranges from casual Facebook and Twitter discussions to starting your own sustainable science group or practicing your writing skills for the NESSE blog. For more information about NESSE and to join the community, please visit their website at http://www.sustainablescientists.org/ NESSE is on Twitter (@greenscientists) and Facebook https://www.facebook.com/groups/sustain ablescientists/ For any further questions email, Ray Borg, a graduate student at UMass Boston, and also a current active member of NESSE at: GreenChemNewsletter@umb.edu This Issue of UMB Green Chemistry Newsletter was brought to you by: Caitlin Pollock and Ray Borg If you are interested in joining our mailing list please contact Caitlin Pollock at: GreenChemNewsletter@umb.edu UMB GreenChemistry 3