Michael Haley – UOregon Chemistry

In my happy place—garden 2026 is in the ground! While it's only the beginning of March, winter has skipped Oregon this year. I've planted cool weather veggies–arugula, mizuna, lettuce, mixed greens, onions, bok choy, spinach, maché and garlic. Tomato starts are in the windowsill of my bedroom!

Aromatic Interactions Select for Homodimeric Assembly in a Quadruply Hydrogen-Bonded DADA 1,2-Azaphosphinine Dimer Inclusion of a fused pyridine ring onto the core motif of an azaphosphinine heterocycle, as well as functionalization with an N-acetamide group, furnishes a chiral, quadruple hydrogen bonding face that is capable of strong homodimerization. Eleven different azaphosphinine derivatives were prepared with variable electron donor and acceptor functionalization. Contrary to simple DA azaphosphinine dimers, trends from substituent effects showed that the hydrogen bond acceptors (A) were more sensitive to the substituents than the hydrogen bond donors (D). With electron donating groups appended onto the azaphosphinine scaffold, dimerization constants rose to as high as 209 M–1 in 10% DMSO-d6 in water-saturated CDCl3. X-ray crystallographic data unexpectedly showed that the quadruply hydrogen bonding system preferred the theoretically less stable donor–acceptor–donor–acceptor (DADA) H-bond orientation despite having the capability to tautomerize to the potentially more stable DDAA structure. Computational analysis revealed that maintaining pyridine aromaticity was more stabilizing than the secondary interactions that would be created from a DDAA dimer. Additionally, these molecules associate as the first examples of R,R- and S,S-azaphosphinine homodimers, compared to the R,S-heterodimers typically found for simple azaphosphinines. This observation was explained by computational analysis, which found a geometric difference between the nitrogen atoms adjacent to the phosphorus chiral center of the Homo and Hetero dimer, leading to a stronger hydrogen bonding interaction in the Homo dimer. Further understanding of this quadruply hydrogen bonding core will allow us to explore further applications that integrate this strongly hydrogen bonding system into larger and more complex supramolecular frameworks such as supramolecular polymers or capsules.

At long last—a GREAT effort by Megan & Nolan finally out in JACS after a 2+ year gestation. We found quadruply hydrogen-bonded DADA azaphosphinine homodimers are preferred over the theoretically more stable DDAA dimers, and they possess STRONG homodimerization constants.
pubs.acs.org/doi/full/10....

The "Designed π-Systems" symposium at Pacifichem2025 is a wrap! Having been on the organizing team since 2005, it’s time for new blood. I have zero doubt that Aiko, Ramesh, and Wes will do a great job. While bittersweet, I "ride off into the sunset" knowing that this symposium will be in good hands!

Aloha from the big island of Hawaii - road trip circumnavigating the northern half of the island today before our Pacifichem symposium later in the week. Incredible scenery - happy students, happy advisor! Importantly, the weather cooperated - mostly. Alternating between clouds and sun - no rain!

The interplay of antiaromaticity and diradical character in diarenoindacenes and diindenoarenes Over the past ∼15 years our group has performed multiple structure/properties relationship studies to assess how logical structural refinement can affect the antiaromaticity/diradicaloid continuum. Us...

Now out in Chem. Sci., 15 years of chemistry distilled down to 22 pages – my group's magnum opus. Great job by Efrain, Gabby & Josh! Many thanks to
@aromaticist.bsky.social, @judywuchem.bsky.social, Juan Casado, Carlos Gomez-Garcia & myriad other collaborators.
pubs.rsc.org/en/content/a...
#pisky

Sake is the cure

Hmmmm.... it would seem to me this company needs to hire someone to "prroofread" their marketing emails....

ACS announces 2026 national award winners The winners are being acknowledged for their outstanding achievements in chemistry across various fields in the discipline

BIG congratulations to my longtime collaborator, conference organizer co-conspirator, and very dear friend @mpetrukhina.bsky.social for winning the George A. Olah Award in Hydrocarbon & Petroleum Chemistry. Well deserved!!! 👏 🎉 🥂

ACS announces 2026 national award winners cen.acs.org/people/award...

Yukon gold harvest time – 10+ pounds of 'taters from one wine barrel – not too shabby! The first pic was from 4 weeks ago. The tops had died back to very few leaves, which suggested that it was time to harvest. The other wine barrel has green beans, which I have been enjoying since mid-May.

New grant means finally updating supplies and equipment in the lab. I cannot recall the last time we bought heating mantles... clearly, it was long overdue, but the one on the right still works!

Garden 2025 looking great!!! A bit behind this year but I don’t care!

And to the one nay-sayer who emailed me this morning, I did NOT post this notification to gloat. Rather, I wanted/needed to show to the #ChemSky community that NSF grant $$$ continue to flow.

One of the most important emails I have received for 2025. THANK YOU to the reviewers and panelists of our NSF proposal for believing in my group's scientific endeavors on PN-heterocycles (azaphosphinines) one more time. This will provide research funds for my group until fall 2028. #chemsky #pisky

Big congratulations 🎊🍾🎈 to Dr. Efrain Vidal Jr., the newest PhD from the Haley Lab at UO. Super happy to get this one over the goal line - excited to see what comes next in his career! On the flip side, he is the very last student on the IF project ☹️…

Osmium ensnared in a hydrocarbon ring Chemists make new class of planar organometallic compounds

An ABSOLUTELY spectacular structure by the Xia group at SUSTECH. Haiping & his team have been working on enveloping the metal with a fully conjugated carbon ring for over a decade, and they finally succeeded! This warms my reformed metallabenzene chemist's heart!
cen.acs.org/synthesis/Os... #PiSky

Complete garden 2025 ready to go into the ground ANY day now. A couple more days of nice and sunny 70F weather like this and I am pulling the trigger! #chemistswhogarden

April is “plant starts in every window sill” month—tomatoes, peppers, cucumbers, squash, eggplant, tomatillos, and beans. I'm only missing a few peppers and some basil—essentially a whole garden waiting until it is warm enough to plant outdoors. Salad greens are outside already. #chemistswhogarden

🌟 Abstract Submission and Registration are Open!!! 🌟
Join the 6th International Symposium on Curved Organic π-Molecules & Materials (CURO-π6), 23–25 July 2025 in St. John's, NL, Canada. Network, collaborate & explore innovations!

#CUROπ6 #ISNAFamily #MemorialUniversity

Come join us at Pacifichem 2025 in Hawaii this December! We have a great group of Invited Speakers and room for a number of Contributed Talks. It should be an excellent 2.5 days (December 18-20) of science!

A windowsill full of tomato starts!

Something tells me that I am going to have PLENTY of tomato starts to share later this spring! These babies are Mortgage Lifters and San Marzano Gigante. Other window has Bicolor Beefsteak and Better Boy seedlings. Planted spinach, lettuce, & bok choy starts outside this morning. #chemistswhogarden

Yet again, our professional chemistry societies take advantage of their hapless members. I reserved on Expedia 3 studio apts located 5 minutes away from the Hilton Hawaiian Village (where our symposium takes place) for $209/night. Room includes kitchenette, king bed & queen bed – nuff said. #ripoff

Garden 2025 is off and running! Lots of early season greens (bok choi, spinach, lettuces, etc) under the grow lights and 160(!) tomato seeds planted this afternoon. I’ll give most of the tomatoes away but better safe than sorry to excess plants than too few - not wanting to repeat 2021s die off.

This is absolutely ABSURD! A "discounted" rate of $334 per night plus taxes??? The American Chemical Society should be embarrassed by these housing prices, along with their high registration prices. Save your money and go to a GRC meeting and get so much more out scientifically. #chemsky

Great day on the Oregon coast and hiking in the coast range with ⁦@aromaticist.bsky.social and Holger Bettinger. Cool but wonderfully sunny. We even saw a herd of 30-40 elk! The hike got cut short before we could reach the top of the waterfall section as you can see the damaged bridge above my head.

Agreed, but a new PI or a PI at a small school may be less knowledgeable on how the game is played. All it takes is one unfortunate soul out out a thousand calls to = $$$

Not to mention that it is after 8PM on a Friday in D.C. Like anyone will call that late??? BTW, the Area Code was 254, which is in Texas, so DEFINITELY not NSF!

I just got a voicemail of one of these calls from a "Mae Amor". It sure did not sound like any NSF Program Manager I know. What scum! #chemsky

Happy to report some 14 days after his emergency spinal surgery, RB2 got his staples out this afternoon. Vet was very pleased by his progress. Gonna be a wicked scar but who cares? Still on painkillers and sedatives for a few more weeks, but he will power through!

What few there are are targeted, but a general program for PDFs at NSF does not exist