CCE Newsletter Winter 2022 Website

CCE Newsletter winter 2022

Welcome Message from The Chair, Dennis Dougherty

Happy new year! We hope the holiday season was a restful time for you and your family. Despite its challenges, the fall term went well for CCE. We held almost every class in person with the largest and most diverse class of students ever. Our virtual CCE Seminar Day was a rousing success, with outstanding work by May Zeng, Sepand Nistanaki, Joseph Derosa, and Steve Kim being singled out for recognition. You can view some of the posters below. We celebrated National Chemistry Week with the Caltech Y’s Rise Program and an interesting battery demonstration in line with the theme “Fast or Slow…Chemistry Makes It Go!” Students from local public schools had a fun and engaging demonstration by graduate student Christopher Povinelli from Kim See’s lab. We celebrated Manni He, recipient of the 2021 Barbara J. Burger Graduate Fellowship. Manni is a fourth-year graduate student in Scott Cushing’s lab focusing on developing high-flux ultra-broadband entangled photons for biosensing applications. Read more about her work below. We welcomed back to Caltech Karthish Manthiram who joined CCE as Professor of Chemical Engineering and Chemistry. Read more about his lab’s work on the molecular engineering of electrocatalysts below. Our research spotlight this quarter features work by May Zeng, the Shapiro Lab, and graduate student Olivia Harper Wilkins.

In early November, we bid farewell to the Clifford S. and Ruth A. Mead Memorial Undergraduate Chemistry Laboratory to make way for the new Resnick Sustainability Institute. When it was constructed, the Mead Laboratory was the most advanced undergraduate chemistry teaching lab in the country. This newsletter features the original Caltech News article about the Mead Lab as well as a photo of Arnold Beckman at the dedication in 1982. In other facilities news, we completed the renovation of the Hartley Memorial Seminar Room in Spalding Laboratory 106.

In DEI news, we celebrated the ribbon cutting for the Donald Alstadt Workshop with Judy Alstadt and Professor Harry Gray. The endowed workshop will send faculty and students to colleges to attract underrepresented and low-income students. We also held a series of two DEI Town Halls. The first one was recorded, and a link is given below. The second Town Hall was a collection of breakout rooms with smalls groups of people making actionable recommendations. We look forward to presenting the DEI Committee’s report on these Town Halls in a future newsletter.

Finally, the Division, and indeed the world of chemistry, was greatly saddened by the passing of Bob Grubbs. Bob was an amazing scientist, and an even more amazing person. He is truly irreplaceable. Many have asked about plans to celebrate Bob’s life. I have been talking with the family, and I do anticipate that sometime in the future there will be a memorial service on campus. We will keep you informed.

With the busy fall term behind us, we look forward to an exciting and productive winter term, with the hope that we will be able to gather together again soon.

In Memoriam: Robert (Bob) Grubbs

Caltech Mourns the Loss of Nobel Laureate Robert H. Grubbs

LA Times: Robert H. Grubbs, Caltech Nobel Prize winner who revolutionized green chemistry, dies

To contribute to the Grubbs Fellowship please visit the Bob and Helen Grubbs Fellowship page.

CCE SEMINAR DAY

CCE Seminar Day was held on Thursday, October 21. Graduate students and postdoctoral scholars presented short talks for a day-long celebration of exceptional research occurring throughout the division. It was followed by a poster session held on Gather.town. Presentations winners were annouced:

Oral Presentations:

Session 1: May Zeng
Session 2: Sepand Nistanaki
Session 3: Dr. Joseph Derosa
Session 4: Steve Kim

Posters:

Jordan Thompson

The grayannanes are a class of natural products that contain a diverse array of biological activities. Despite how long scientists have been aware of compounds from this class, there is an alarmingly low amount of syntheses. We are interested in achieving the first total synthesis of Auriculatol A, which was isolated in 2018 and is a potent inhibitor of sodium ion channels and human carbonic anhydrase II. Our strategy utilizes an alpha-enolate arylation of a lactone or silyl ketene acetal and vinyligous mukaiyama aldol of a particularly hindered substrate. We have achieved a late stage alpha enolate arylation to construct the central 7-membered ring, albeit in low yield. Following optimization of this reaction, we envision an efficient end-game strategy consisting of a birch reduction, allene [2+2], and samarium diodide mediated rearrangement.

Caiyou Chen

The substitution of an alkyl electrophile by a nucleophile is a foundational reaction in organic chemistry that enables the efficient and convergent synthesis of organic molecules. Although there has been substantial recent progress in exploiting transition-metal catalysis to expand the scope of nucleophilic substitution reactions to include carbon nucleophiles, there has been limited progress in corresponding reactions with nitrogen nucleophiles. For many substitution reactions, the bond construction itself is not the only challenge, as there is a need to control stereochemistry at the same time. Here we describe a method for the enantioconvergent substitution of unactivated racemic alkyl electrophiles by a ubiquitous nitrogen-containing functional group, an amide. Our method uses a photoinduced catalyst system based on copper, an Earth-abundant metal. This process for asymmetric N-alkylation relies on three distinct ligands—a bisphosphine, a phenoxide and a chiral diamine. The ligands assemble in situ to form two distinct catalysts that act cooperatively: a copper/bisphosphine/phenoxide complex that serves as a photocatalyst, and a chiral copper/diamine complex that catalyzes enantioselective C–N bond formation. Our study thus expands enantioselective N-substitution by alkyl electrophiles beyond activated electrophiles (those bearing at least one sp- or sp2 -hybridized substituent on the carbon undergoing substitution) to include unactivated electrophiles.

Linh Le (People’s Choice award)

Nitrogen, a common component of biomolecules, is sourced from abundant dinitrogen in the atmosphere through conversion to ammonia. Organisms capable of fixing N2 employ nitrogenases, metalloproteins that display metal-sulfide clusters that facilitate electron transfers and substrate activation. The site of N2 conversion to NH3 is FeMco (M = Mo, Fe or V), a cluster of notable complexity in bioinorganic chemistry, which displays an unusual interstitial carbon ligand. The function of this bridging ligand remains unclear, and systematic structure-function studies with bridging C-donors are challenged by lack of synthetic methods for analogous clusters. Herein, we report the first synthetic cluster that models a cubane moiety of FeMco bearing a chelating carbyne ligand and related structure-property studies that show a substantial impact on reduction potentials.

National Chemistry Week Demonstration

This year's National Chemistry Week was celebrated October 17–23 with the theme, "Fast or Slow...Chemistry Makes It Go!"

On October 21st, Caltech Y Rise Program students learned about chemical current sources and reaction rates with graduate student Christopher Povinelli, from Kim See’s lab, at the Hameetman Center.

2021 Barbara J. Burger Graduate Fellowship Recipient: Manni He

Manni He is a fourth year PhD student in Professor Scott Cushing’s lab. Her research focuses on developing high-flux ultra-broadband entangled photons for biosensing applications. By harnessing the non-classical properties of entangled photons, she is working to miniaturize nonlinear spectroscopies for in situ studies as well as develop novel noninvasive optical imaging techniques.

The Burger Fellowship provides a female chemistry graduate student in at least her fourth-year with an interest in pursuing a career outside of academia a partial stipend support and $3,500 in research funds.

NEW FACULTY

Dr. Karthish Manthiram

Karthish received his bachelor’s degree in Chemical Engineering from Stanford University and his Ph.D. in Chemical Engineering from UC Berkeley. As a graduate student in Professor Paul Alivisatos’ group, Karthish developed transition-metal oxide hosts for redox-tunable plasmons and nanoparticle electrocatalysts for reducing carbon dioxide. During his postdoctoral research in Professor Robert Grubbs’ lab at Caltech, Karthish developed new anion-exchange ionomers. Karthish joined the MIT faculty as an Assistant Professor in 2017. In 2021, he officially joined CCE as Professor of Chemistry and Chemical Engineering. The Manthiram Lab is focused on the molecular engineering of electrocatalysts for the synthesis of organic molecules, including pharmaceuticals, fuels, and commodity chemicals, using renewable feedstocks.

Building a Synthetic World from Thin Air

Research Spotlight: Robb Lab

5-Aryloxy substitution enables efficient mechanically triggered release from a synthetically accessible masked 2-furylcarbinol mechanophore

Polymers that release small molecules in response to a specific stimulus are appealing materials for a range of applications including drug delivery, sensing, catalysis, and self-healing. Polymers incorporating force-responsive molecules known as mechanophores enable the release of covalently-bound cargo molecules upon mechanical stimulation with excellent selectivity and control. Previous research in the Robb group has established a mechanophore platform based on masked 2-furylcarbinol derivatives that are capable of releasing small molecule payloads through a mechanically triggered retro-Diels–Alder/fragmentation–decarboxylation cascade. Recently, research led by graduate student Tian Zeng and postdoctoral scholar Xiaoran Hu identified an improved mechanophore design that is accessed through a robust, four-step synthesis while maintaining excellent payload release activity. An aryloxy group at the 5-position of the masked furan simultaneously serves as a convenient handle for polymer attachment as well as an electron-donating substituent to accelerate cargo release after mechanical activation.

Research Spotlight: Shapiro Lab

In this study, we showed that we could turn genetically engineered cells into ultrasound-triggered "bombers" by having them express gas vesicles and using focused ultrasound to "explode" these vesicles into tissue-damaging and drug-releasing bubbles. We used this approach with tumor-infiltrating bacteria, activating them with focused ultrasound inside tumors to damage the tumor and promote anti-tumor immune responses.

Nature Nanotechnology: Acoustically triggered mechanotherapy using genetically encoded gas vesicles

Popular Science: Researchers are using gassy, explosive bacteria to destroy cancer cells

Research Spotlight: Olivia Harper Wilkens

"“I wrote Astrochemistry for someone who was like myself when I was starting grad school: a chemist trying to break into astronomy not having taken an astronomy course. I had an idea to write and illustrate a book about the molecular universe. I talked it over with Caltech librarian Donna Wrublewski, who contacted people in ACS [American Chemical Society] publications. They decided it would be perfect for their new digital ACS In Focus series. Then, I told my research adviser, Geoff Blake, about the project. He was really supportive and agreed to be my mentor; the In Focus books pair early-career researchers with more senior mentors as co-authors. I consulted his cosmochemistry notes, and he was helpful in outlining the book. We had a lot of conversations. I wrote the text and contributed illustrations, and the book, which is digital, takes advantage of the ability to integrate videos, animations, and interviews with experts alongside the text. I’m excited that readers will be able to see different processes play out as they read about them, and I hope the interviews will be especially helpful in sharing different aspects of astrochemical research while also serving as a sort of time capsule for the field."

Read the full story from Caltech Magazine's #SoCaltech Series

Meet Dr. Kimberly Papadantonakis

Kimberly earned a B.S. in Forensic Science from the City University of New York John Jay College of Criminal Justice in 2002, and a Ph.D. in Chemistry from the California Institute of Technology in 2008. After finishing her Ph.D., she joined the research staff of the Institute for Defense Analyses in Alexandria VA. In 2013 she returned to Caltech as the Scientific Research Manager for the Lewis group, where she led successful proposal-writing efforts, contributed to electrochemical and materials research, helped compose manuscripts, managed finances, and completed grant reports. The CCE Division Office welcomed Kimberly in March 2021 in order to provide a resource to the entire division for assistance with grant writing, project management, and other tasks that require technical writing skills. Reach out to Kimberly (kimberly@caltech.edu) for help with any and all proposals.

FACILITY UPDATES

Mead Laboratory Demolition

On November 2, 2021, the CCE community bid farewell to the Mead Undergraduate Laboratory. Mead Lab was demolished to make way for the new Resnick Sustainability Institute building.

CCE Chair, Dennis Dougherty talks with Professor Harry Gray-- who was CCE chair when Mead Laboratory was established.

CCE faculty and staff gather to celebrate Mead Laboratory's legacy.

History of Mead Laboratory

(Left Photo) Front page of 1982 Caltech News Article. (Right Photo) Arnold Beckman at the Mead Lab Dedication dedication

Dedicated on April 19, 1982, the Clifford S. and Ruth A. Mead Memorial Undergraduate Chemistry Laboratory was built to fulfill a new demand for undergraduate labs after the February 1971 earthquake damaged Gates Laboratory. With a new building came a transformation of curriculum that required modern instrumentation, thus resulted "the most sophisticated undergraduate lab in the country in terms of structure, instrumentation, and curriculum" at the time. Mead Lab was named in honor of Pasadena businessman Clifford S. and Ruth A. Mead who's estates funded the project.

Read the December 1982 Caltech News Article about Mead Lab

Official Mead Lab Dedication Program

106 Spalding Lecture Hall

The Fred L. Hartley Lecture Hall, the main lecture hall in the Spalding Laboratory, was updated during the winter holiday break. When in-person classes resume, students and faculty will find new chairs, newly painted walls, updated ceilings and lighting.

CCE DEI Updates & News

Donald Alstadt Workshop

In October, we celebrated the Donald Alstadt Workshop with Judy Alstadt and Professor Harry Gray. Part of the Division of Chemistry and Chemical Engineering’s Future Ignited program, the workshop will send Caltech faculty and students to colleges, where they will provide undergraduates with insights about their work to encourage a career in research. The aim is to attract aspiring scholars from underrepresented and low-income backgrounds to careers in science and engineering.

Joining them are CCE Division Chair, Professor Dennis Dougherty, Mickey and Kaya Pohl, Robert Schlaudecker, Carolyn Sennett, Shirley Gray, Partners at Jones Day Steve Corr, Andrea Jeffries, and Lexi Smith.

Visit here for more information about the Donald Alstadt Workshop.

CCE DEI Town Hall Meetings

On November 15th, the CCE community was invited to participate in a two part DEI Town Hall series hosted by The Chemistry Graduate Student Council (CGSC) to update the community on the division's efforts to improve diversity, equity, and inclusion within and outside of CCE.

In the first event, Guest speakers included members from CCID, CGSC, DICI, PRISM+, WiC, and faculty, who discussed initiatives that they led over the previous and current academic year.

The second event was an opportunity to reflect on the division's DEI progress and to discuss ideas to improve upon current DEI initiatives. Attendees were encouraged to provide reflection, feedback, and brainstorm ways to improve retention, recruitment, and promotion of DEI initiative.

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