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Recent Graduate Discovers New Class of Recyclable Thermosetting Materials



Thermosetting plastics are the strongest class of materials that can be synthesized, they are defined as a type of polymer that "set"s irreversibly with heat. Due to their rigidity and low density (versus metals), they are commonly utilized as plastics for the manufacturing of structural composites (for airplane and auto parts), adhesives, and microelectronics. Inherent chemical inertness, a property needed for longevity and robustness, of the polymers, has one drawback: thermosets typically cannot be recycled or reworked. Accordingly, parts manufactured with defects must be discarded, costing industry millions of dollars and contributing to toxic waste build up.

Dr. Jeannette (Jamie) Garcia (formerly O’Brien), a recent graduate of our doctoral program and former member of Professor Amir Hoveyda's group, and her colleagues at IBM Almaden have made an exciting discovery that might provide an effective solution to the above problems. Based on a serendipitous discovery arising from exclusion of a reagent in a reaction mixture to prepare a known thermosetting polymer, Dr. Jamie Garcia has uncovered a new class of thermosetting materials that are recyclable. The chemistry, details of which appeared recently in a paper in the journal Science http://www.sciencemag.org/content/344/6185/732.full, for which Garcia is one of the two principal authors, entails polycondensation of diamines with paraformaldehyde to poly(hexahydrotriazine)s (PHTs); the presence of a catalyst is not required and the monomers are inexpensive. Computation (DFT calculations) and small-molecule studies enabled the IBM team to elucidate the mechanism of the polymer-forming process. From these studies, they learned that the thermoset could be selectively reverted to monomer at low pH. The chemical reversibility appears a consequence of the reversibility of the hexahydrotriazine core, which hydrolyzes selectively in strongly acidic aqueous conditions. This is the first example of a completely recyclable thermosetting polymer and may offer a new approach to stimuli-responsive recycling.

Guided by their mechanistic understanding, Garcia and co-workers have identified a solvent-stabilized intermediate poly(hemiaminal) that, when a flexible oligomeric diamine is used as monomer, an elastic organogel forms which can be reverted in neutral water. The combination of covalent and hydrogen bonds in the hemiaminal dynamic covalent network (HDCN) allows the gel to exhibit a property called "self-healing"; that is, if the gel is cut into segments and recombined, the parts instantly reform a cohesive gel. Because of its reversibility, this advance might find applications in cargo delivery, such as the slow release of perfumes, dyes or therapeutics. What is more, the self-healing properties of the gel may be attractive for use as adhesives that instantly forms a firm bond on contact without heat or drying.

For additional commentary see: The New York Times http://www.nytimes.com/2014/05/16/science/error-leads-ibm-researchers-to-a-new-family-of-materials.html?hpw&rref=technology&_r=0
(05.20.14)


Amir Hoveyda receives the 2014 ACS Award for Creative Work in Synthetic Organic Chemistry sponsored by Aldrich Chemical Co.

Amir H. Hoveyda

Professor Amir H. Hoveyda, the recipient of the 2014 ACS Award for Creative Work in Synthetic Organic Chemistry, was honored at the Awards Ceremony on March 18, held in conjunction with the ACS National Meeting in Dallas, Texas.

First established in 1955 to recognize and encourage creative work in synthetic organic chemistry, this major award from the ACS has been sponsored by the Aldrich Chemical Co. since 1976. The award includes a cash prize which consists of $5,000 and a certificate.

The citation for the award reads: “For his design and development of new, selective, and highly powerful catalytic transformations and their application to total synthesis of complex molecules of biological significance.”

Dr. Hoveyda is the Joseph T. and Patricia Vanderslice Millennium Professor of Chemistry at Boston College and currently serves as chair of the Department of Chemistry.

(05.09.14)


2013 -2014 Graduate Fellowships

(L-R) Fanke Meng, Zhiyong Yu, and Hilan Kaplan.

Five graduate students have received graduate fellowships for this academic year.  John LaMattina Graduate Fellowships were awarded to Hilan Kaplan (Byers Group) “Synthesis and Characterization of Bis(imino)-N-Heterocyclic Carbene Complexes of Iron for Polymerization and Catalysis,” Fanke Meng (Hoveyda Group) “Cu-catalyzed Synthesis of Boron-substituted Allylcopper Complexes and their In Situ Itilities in Organic Synthesis”, and Zhiyong Yu (Morken Group)  “An Efficient Synthesis of (+)–Discodermolide: Target Inspired Reaction Development”

(L-R) Rana Kashif Khan and Michael Ardolino.

Recognized for their achievement in organic chemistry, Michael Ardolino (Morken Group) “Methodology Development and Mechanistic Studies on Palladium-catalyzed allyl-allyl and allyl-propargyl Cross Couplings" and Rana Kashif Khan (Hoveyda Group) for his project that deals with the development of Ru-based catalysts to promote highly efficient and Z-selective olefin metathesis reactions and the mechanistic elucidation of such transformations are recipients of the AstraZeneca Graduate Fellowships in Organic Chemistry.
(04.29.14)


Professor Liu honored as Organometallics Young Investigator

Shih-Yuan Liu

In recognition of his impact on scientific research in organometallic chemistry, Professor Shih-Yuan Liu is the recipient of a 2014 Organometallics Young Investigator Fellowship.  He will be presenting a talk at the Organometallics Symposium held during the Fall 2014 ACS meeting in San Francisco this August.
(03.17.14)




Thomas Kempa  - IUPAC Prize Winner

Dr. Abhishek Chatterjee

Thomas Kempa, a BC ’04 chemistry undergraduate, was the sole American winner of the 2013 IUPAC Prize for Young Chemists.  Established to encourage exceptional research scientists at the start of their careers, this Prize is given for the most outstanding Ph.D. theses in the chemical sciences.  While at Boston College, Dr. Kempa completed the honors chemistry curriculum and worked in the research laboratory of Professor John Fourkas.  He received his Ph.D. at Harvard University under the advisement of Professor Charles Lieber and is currently a post doc in the Nocera Lab at Harvard.
(10.08.13)



Dr. Abhishek Chatterjee Joins Chemistry Faculty

Dr. Abhishek Chatterjee

We are pleased to announce that Dr. Abhishek Chatterjee has joined the Chemistry Department faculty. A chemical biologist, he received his postdoctoral training at The Scripps Research Institute in the research group of Professor Peter G. Schultz. He received his Ph.D. at Cornell University under the direction of Professor Tadhg Begley.

Dr. Chatterjee’s independent research program will focus on developing and applying novel chemical-biology approaches to “probe and engineer complex biological systems.”
(9.12.13)


2013 Chemistry Department Student Awards

At the Student Awards Ceremony, graduate students and undergraduate Chemistry and Biochemistry majors received special recognition. See the complete list of award recipients >>.
(7.2.13)


McCarthy Prize Awarded to Chemistry Graduate Lamontagne

Leo Lamontagne

Leo Lamontagne, BS ’13, who performed research in the laboratory of Professor Frank Tsung was awarded the McCarthy Prize for his Scholar of the College thesis, “Synthesis of Morphologically Controlled Core-Shell Au-Pd Nanoparticles and Their Electrocatalytic Activity Toward Formic Acid Oxidation.”  Students receiving the distinction of Scholar of the College have excellent academic records and work independently, under the supervision of a faculty advisor, during their senior year.  Awarded by the Deans of the College of Arts & Sciences, the McCarthy Prize recognizes the best Scholar of the College theses. Lamontagne will be continuing his studies in pursuit of a doctoral degree in the Materials Science and Engineering Department at the University of California, Santa Barbara.
(5.24.13)


Professor Udayan Mohanty named a Fellow of the Royal Society of Chemistry

Professor Udayan Mohanty

Professor Udayan Mohanty has been named a Fellow of the Royal Society of Chemistry (FRSC).  FRSC Fellowships are awarded to scientists who have made either exceptional contributions to the profession, the advancement of the field or direction of an organization involved with chemistry.

Professor Mohanty is known for his work in the fields of physical chemistry, chemical physics, and biophysics. He has done fundamental work in interactions of ions with nucleic acids, molecular motions of liquids below the freezing point, density wave theory of solid-liquid transition, dynamics of nucleic acids in gels and free solution, systems away from equilibrium and stochastic process, and density functional theory of quasi-crystals.

Read an article about Professor Mohanty from the BC Office of News & Public Affairs
(4.11.13)


Professor Shih-Yuan Liu Joins Chemistry Faculty

Shih-Yuan Liu

The department is pleased to announce the appointment of Professor Shih-Yuan Liu to the chemistry faculty at Boston College. Professor Liu is currently an associate professor of chemistry at the University of Oregon and is best known for his pioneering research on azaborines – benzene rings in which a C=C bond has been replaced by a B=N bond. Azaborines closely match the size and shape of ordinary benzene rings, and they still enjoy considerable aromatic stabilization, but most of their other physical, chemical, and spectroscopic properties are significantly altered.

Professor Liu is currently studying azaborines as high-capacity hydrogen storage materials, as novel optoelectronic materials, and as electronically-modified isosteres of drugs and other biologically active compounds. In 2012, Professor Liu won both a Camille Dreyfus Teacher-Scholar Award and the Journal of Physical Organic Chemistry Award for Early Excellence. He will join the BC faculty this summer as a full professor of chemistry.

(3.25.13)


NSF Graduate Research Fellowship Awarded to Ashley Biernesser

Leo Lamontagne

Ashley Biernesser, a graduate student in Professor Jeffery Byers' research group, has received a prestigious National Science Foundation Graduate Research Fellowship. Awarded to senior undergraduate and first or second year graduate students, this fellowship invests in an individual’s potential by affording an opportunity to pursue his or her research aspirations. Fellows receive a three year annual stipend of $30,000. Ashley’s current project is “Iron pyridyl diimine catalysts for the production of a tunable biodegradable polymer."
(4.3.13)




Recipients of 2012-13 AstraZeneca Graduate Fellowships in Organic Chemistry Named

Sun & Silverio
2012-13 AstraZeneca Graduate Fellowships in Organic Chemistry
(L-R) Xixi Sun and Dan Silverio.

Dan Silverio and Xixi Sun, graduate students in the research laboratories of Professors Amir Hoveyda and Kian Tan respectively, have been named the 2012-13 AstraZeneca Graduate Fellows in Organic Chemistry. Sun’s research is focused on catalysts applying reversible covalent bonding and their applications towards site-selective functionalization of diols and carbohydrates.  Dan Silverio has been working on the development of new catalysts for the enantioselective synthesis of amines and alcohols.  This award is given to senior graduate students who intend to pursue a career in industry, have published papers in recognized chemistry journals and presented their work at external conferences.  Candidates selected for this honor are further evaluated on their research acumen and scholarship.
(9.5.12)


Ardolino receives 2012-13 ACS Organic Chemistry Division Fellowship

Michael Ardolino

Michael Ardolino, a graduate student in Professor James Morken’s group, is the recipient of a 2012-13 Graduate Fellowship awarded by the Division of Organic Chemistry of the American Chemical Society. The fellowship is highly competitive and recognizes “outstanding third and fourth year graduate students in organic chemistry." Ardolino will receive a fellowship stipend of $26,000 which includes funds to travel to the 2013 National Organic Symposium which will be held in June at the University of Washington. His research is focused on development of new asymmetric transition metal-catalyzed methodologies for the manipulation of allylic and related systems.
(9.5.12)



John LaMattina Graduate Fellowships Awarded

LaMattina Graduate Fellows 2012
2012 John LaMattina Fellows, (L-R) Victor Rendina, Candice Joe, and Chris Schuster.

John LaMattina Graduate Fellowships have been awarded to Candice Joe, Rana Kashif Khan, Victor Rendina and Chris Schuster. Joe, a member of Professor Kian Tan's group, is currently involved in the design and synthesis of new enantiopure scaffolding ligands for asymmetric hydroformylation of other interesting substrate classes. Working in the research group of Professor Amir Hoveyda, Khan (not pictured) is investigating the mechanism of olefin metathesis promoted by stereogenic-at-Ruthenium carbene complexes, and development of new catalysts to access Z-alkenes. A member of Professor Marc Snapper’s group, Rendina is currently developing a new class of chiral cationic organocatalysts for use in a variety of asymmetric alkylation reactions.

In Professor James Morken’s group, Schuster’s research focuses on engaging enantioenriched 1,2-diboron compounds as nucleophilic partners in selective cross coupling reactions.
(9.5.12)


Fang Gao named recipient of the 2012 Graduate Student Innovation Award (GSIA) by the Sigma-Aldrich Company

Fang Gao, a graduate student in the research lab of Professor Amir Hoveyda, has been awarded a 2012 Graduate Student Innovation Award (GSIA) by the Sigma-Aldrich Company.

Sigma-Aldrich gives these awards annually to students who have completed three years of graduate study for work that focuses on the "development and creative use of current or new reagents, catalysts, and ligands in methodology or synthetic chemistry projects."   Recipients will receive a $1,000 award, an iPad 3, and an all-expense paid trip to the 2012 GSIA Symposium at the Aldrich campus in Milwaukee, Wisconsin.  All Awardees are invited to give a short presentation on their research at the Symposium.
(8.7.12)


Professor L. T. Scott named Fellow of the American Chemical Society

Professor Lawrence T. Scott has been named a Fellow of the American Chemical Society. The formal announcement appeared in the July 23, 2012 issue of Chemical and Engineering News:
http://cen.acs.org/articles/90/i30/2012-ACS-Fellows.html

With over 164,000 members worldwide, the American Chemical Society ranks as the largest single-science professional society in the world. The Fellows Program was inaugurated in 2009 “to recognize members of the ACS for outstanding achievements in and contributions to Science, the Profession, and the Society.” Fewer than 1% of the members of the ACS have been named Fellows of the Society.

Professor Scott joined the faculty at Boston College in 1993 and currently occupies the Louise and Jim Vanderslice and Family Chair in Chemistry. He is best known to scientists for his development of laboratory methods for the chemical synthesis of carbon-rich materials such as C60, higher fullerenes, carbon nanotubes, and novel graphene substructures. He currently serves as chair-elect for the ACS Division of Organic Chemistry and sits on the editorial advisory board for The Journal of Organic Chemistry. Since 2006, he has served also as associate chair of the BC chemistry department.
(7.23.12)


Chemistry Department Awards Ceremony

The annual department student award ceremony, held on May 4th, recognized the undergraduate and graduate honorees. A complete list of the winners may be viewed here.
(5.4.12)


Professor Kian Tan's No. 1 Video at the ACS National Meeting Fall 2011

Professor Kian Tan's presentation at the ACS National Meeting in the Fall of 2011 was recorded and posted online by the ACS after the meeting.  Over a 7 month period, the presentation was viewed more than 1800 times around the world.  Out of 462 presentations posted from the Fall meeting, Professor Tan's was the No. 1 viewed video.  Because of this, the ACS interviewed Professor Tan about his research program and about the future importance of online presentations to the scientific community. Listen to Professor Tan's interview with the ACS.

To view Professor Tan's presentation, visit: http://www.softconference.com/ACSchem/sessionDetail.asp?SID=267409

To read the interview of Professor Tan, click here.

(4.18.12)


Professor Eranthie Weerapana wins Damon Runyon-Rachleff Innovation Award

Professor Eranthie Weerapana has been awarded the prestigious Damon Runyon-Rachleff Innovation Award for her project “Targeting Reactive Cysteine Residues for Cancer Therapy.” From a highly competitive field of 177, Weerapana was among 5 chosen to receive this honor. This award is designed to support research that is highly inventive and has the potential to influence the way that cancer is prevented, diagnosed or treated. She will receive $450,000 over a 3 year period to support this work.

Professor Weerapana was recently featured in an article in the Boston College Chronicle. (12.15.11)


NSF Faculty Early Career Development (CAREER) Award to Professor Kian Tan

Professor Kian Tan will receive $550,000 over 5 years for work on his project “Application of Reversible Covalent Linkages in Organic Catalysis.” This grant program supports the work of junior faculty who epitomize the role of teacher-scholar by the quality of their research, education and its incorporation into the mission of their organization.
Professor Tan received his doctoral degree from the University of California, Berkeley in 2004 and was an NIH Postdoctoral Fellow at Harvard University from 2004-06.

(12.15.11)


Sa Zhou Captures Silver Award at Materials Research Society Fall Meeting

Graduate student Sa Zhou, a researcher in Professor Dunwei Wang’s group, was the recipient of a Silver Award at the fall meeting of the Materials Research Society (MRS), which was recently held in Boston. This competition is open to domestic and international graduate students in a number of disciplines in addition to chemistry, such as, physics, materials science and engineering. Ms. Zhou is the first Boston College graduate student to win this prestigious award.

(12.15.11)


Smith Family Award for Excellence in Biomedical Research to Professor Eranthie Weerapana

Assistant Professor of Chemistry Eranthie Weerapana has been awarded a Smith Family Award for Excellence in Biomedical Research. Designed to support promising junior faculty who are engaged in new and innovative research in the biomedical sciences, the ultimate goal of this program is the achievement of medical breakthroughs. This prestigious and highly competitive award provides researchers with $300,000 over a 3 year period.

The Weerapana group is utilizing a multidisciplinary approach rooted in synthetic chemistry and mass spectrometry-based proteomics to investigate protein activities that regulate lifespan through the insulin-signaling pathway of the nematode, C. elegans. They aim to gain insight into the molecular basis of aging and define protein targets to aid in drug development efforts to delay the onset of aging and age-related diseases.

Professor Weerapana joined the Boston College Chemistry faculty in September, 2010. She held a Pfizer Post doctoral Fellowship at The Scripps Research Institute after earning her Ph.D. at the Massachusetts Institute of Technology.
(11.17.11)


Professor L. T. Scott to chair ACS Division of Organic Chemistry

Professor Lawrence T. Scott has been named chair-elect for the American Chemical Society Division of Organic Chemistry. His one year term of office will run from January 1 – December 31, 2012. For the 2013 calendar year, he will serve as chair of the division.

With over 150,000 members worldwide, the American Chemical Society is the largest single-science professional society in the world, and the Division of Organic Chemistry, with over 16,000 members, is the largest division within the ACS. Professor Scott has served as an alternate councilor for the ACS, representing both the Division of Organic Chemistry and the geographical region in which Boston College is located, the Northeast Section.

Professor Scott came to Boston College in 1993 and currently occupies the Louise and Jim Vanderslice and Family Chair in Chemistry. Since 2006, he has served as associate chair of the chemistry department.
(10.27.11)


First Annual Boston Women in Chemistry Symposium award Erika Vieira Best Talk

Jeffrey Byers

Erika Vieira, a Ph.D. student in Professor Amir Hoveyda’s laboratory, won the Best Oral Presentation Award at the First Annual Boston Women in Chemistry Symposium. Held at Harvard University, this symposium was established to showcase the excellent work of female chemistry graduate students and post-docs in the greater Boston area. Talks and posters were presented by 50 participants on a wide range of topics. Erika’s oral presentation was entitled “NHC–Cu-Catalyzed Enantioselective Additions of Allyl and Propargyl Groups to Aldimines.” For more information about this event and a collection of photos taken throughout the day, visit: http://www.fas.harvard.edu/~hwic/WInCS/home.html
(10.4.11)


2011-2012 Bristol-Myers Squibb Graduate Fellowship in Synthetic Organic Chemistry awarded to Fang Gao

Jeffrey Byers

Fang Gao, a 5th year graduate student in Professor Amir H. Hoveyda’s group, has been chosen to receive the 2011-2012 Bristol-Myers Squibb Graduate Fellowship in Synthetic Organic Chemistry.

Recognized for their academic and research achievements as well as potential for future accomplishments, Gao in one of five national winners. The others chosen to receive this significant honor represent Scripps Research Institute, Harvard University, Columbia University and UCLA.
(6.30.11)




John Kozarich Summer Undergraduate Research Fellows Named

We are pleased to announce the appointments of the 2011 Kozarich Fellows,  Samantha GoetzLeo Lamontagne and Patrick Wong, as they begin their summer research projects at the Merkert Chemistry Center. With the generosity of Dr. John Kozarich, who endowed the summer fellowship program that bears his name, the department recognizes these exceptional undergraduate researchers in the areas of organic chemistry, chemical biology and physical chemistry.  Biochemistry major Wong ’12 is a student researcher in the lab of Professor Jianmin Gao.  Both Goetz ’13 and Lamontagne ’13 are chemistry majors currently working in the laboratories of Professors Jason Kingsbury and Frank Tsung, respectively.

2011 Kozarich Fellows, (L-R) Patrick Wong, Samantha Goetz, and Leo Lamontagne.

Dr. Kozarich currently serves as chairman and president of ActivX Biosciences, Inc. and was formerly vice president at Merck Research Laboratories. He has also served on the faculty at the University of Maryland and Yale University Medical School. He has over 125 publications and holds three patents. Dr. Kozarich received his B.S. in Chemistry summa cum laude from BC; his Ph.D. in biological chemistry from MIT; and was an NIH postdoctoral fellow at Harvard University. We are grateful for his generous support and inspiration.
(6.2.11)


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