Michael Haley – UOregon Chemistry

@uohaleylab.bsky.social

News/n/views from UOregon Professor Mike Haley 🇺🇸🏳️‍🌈+related chemical research at UO & beyond. Lover of cool science & all chemistry that's pi-electron-rich (#PiSky ⌬). He/him – foodie/vino/travel/gardening/Frenchton owner (or owned by the Frenchton?)

The $h!tshow that is graphyne research... My group stopped working in the this area in 2008. We made big oligomers but not the polymer. Asked today to review yet another manuscript for a top journal & said "NO!" Graphyne, retractions, and bad blood between chemists cen.acs.org/research-int...

Graphyne, retractions, and bad blood between chemists

Professional rivalries in an insular field impede progress for a promising new material

cen.acs.org

Decided this past weekend it was time to pull the trigger, so garden beds 1 & 3 are fully planted – tomatoes, peppers & eggplant in bed 1 and lettuce, fennel, tomatillo, garlic, bok choy & cherry tomatoes in bed 3. Bed 2 still a work in progress... The bok choy this year is delicious!

BildBildBild

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!

BildBildBildBild

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....

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.

pubs.acs.org

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!

Bild

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!

BildBildBildBild

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...

ACS announces 2026 national award winners

The winners are being acknowledged for their outstanding achievements in chemistry across various fields in the discipline

cen.acs.org

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.

BildBildBild

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.

BildBild

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.

BildBild

What a rollercoaster ride the last 72 h – Rocky herniated a disk between his C3-C4 vertebrae, requiring emergency surgery (note staples in neck). After a 40 h recovery, he came home, hopped up on many drugs. Doing great this morning. Expensive surgery ($10K) but my lil’ buddy is WORTH EVERY PENNY!

BildBild