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Mathias Senge

@mathiassenge.bsky.social

Chair of Organic Chemistry - TCD, Hans Fischer Senior Fellow - TU Munich. Organic synthesis, light, structures, porphyrins in all shapes and historical settings

508 Followers  |  125 Following  |  32 Posts  |  Joined: 15.11.2024  |  1.8987

Latest posts by mathiassenge.bsky.social on Bluesky

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The last #WednesdayCoffeeTalk of this summer semester: Florian Egli @tum.de on "The challenge of creating value for all in the global transition towards sustainability".

Part of the IAS Seminar Series of European Universities on Sustainability! DM us for more info.

www.ias.tum.de/ias/news-eve...

21.07.2025 09:45 โ€” ๐Ÿ‘ 2    ๐Ÿ” 1    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0
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It's summer time ๐ŸŒค๏ธand that always means research interns: here are Joe, Syed, and Susan ๐Ÿ˜€. All are locals from our School @tcddublin.bsky.social, Syed is a @rsc.org
#RISE student and Susan has a @rsc.org
#UGResearchBursary ๐Ÿ˜€

21.07.2025 09:53 โ€” ๐Ÿ‘ 12    ๐Ÿ” 1    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0
Bicyclo[1.1.1]pentane is a rigid aliphatic hydrocarbon with a three-dimensional (3D), propeller-like shape and a molecular size which makes it a targeted bioisosteric replacement for phenylene and acetylene groups in medicinal chemistry. For the pharmaceutical application of BCP, simple, efficient, and cost-effective synthetic tools are required to enable the exploration of BCPโ€™s potential as a bioisostere across a broad chemical space. The synthesis of BCP mono- and diketones remains a challenging task, limited by both substrate scope and expensive photocatalysts. Here we present a protocol for Friedel-Crafts acylation of (hetero)aromatic hydrocarbons with BCP acyl chlorides; in particular, the first method to access diaromatic BCP 1,3-diketones. Reaction optimization, substrate scope, and reactivity of the products are discussed. 35 mono- and diketones are reported accompanied by 7 examples of post-synthetic modifications. The synthesis of a BCP analogue of fenofibrate is reported.

Bicyclo[1.1.1]pentane is a rigid aliphatic hydrocarbon with a three-dimensional (3D), propeller-like shape and a molecular size which makes it a targeted bioisosteric replacement for phenylene and acetylene groups in medicinal chemistry. For the pharmaceutical application of BCP, simple, efficient, and cost-effective synthetic tools are required to enable the exploration of BCPโ€™s potential as a bioisostere across a broad chemical space. The synthesis of BCP mono- and diketones remains a challenging task, limited by both substrate scope and expensive photocatalysts. Here we present a protocol for Friedel-Crafts acylation of (hetero)aromatic hydrocarbons with BCP acyl chlorides; in particular, the first method to access diaromatic BCP 1,3-diketones. Reaction optimization, substrate scope, and reactivity of the products are discussed. 35 mono- and diketones are reported accompanied by 7 examples of post-synthetic modifications. The synthesis of a BCP analogue of fenofibrate is reported.

Check out our new #preprint ๐Ÿ“ข๐Ÿ˜€"Bicyclo[1.1.1]pentane Ketones via Friedel-Crafts Acylation" #BCP #isostere @chemrxiv.bsky.social
chemrxiv.org/engage/chemr... great work by Freya and Karolina and coop with #PavelMykhailiuk #EnamineLtd
๐Ÿ‡บ๐Ÿ‡ฆ supported by @researchireland.ie @ias-tum.bsky.social

17.07.2025 08:13 โ€” ๐Ÿ‘ 6    ๐Ÿ” 4    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0
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While rest of us had group meeting in the rain๐ŸŒง๏ธ @tbsi-tcd.bsky.social @tcddublin.bsky.social in Dublin: Karolina, Sophie, and Liam are off into the sun ๐ŸŒžin Salerno at the #SupraChemDays25 meeting showing off cool chemistry โš—๏ธon #porphyrins, #organocatalysis, #atropisomers, #bicyclopentane ๐Ÿ˜€

12.06.2025 18:56 โ€” ๐Ÿ‘ 1    ๐Ÿ” 0    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0

Congratulations to Marike et al. ๐Ÿ‘๐Ÿ‘

10.06.2025 16:20 โ€” ๐Ÿ‘ 1    ๐Ÿ” 0    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0

Happy birthday IAS ๐ŸŽ‰๐ŸŽˆ
A truly unique, supportive and stimulating institute. Best place I ever had the honor to be affiliated with!
And many thanks for the support and kind hospitality over the last few years!

10.06.2025 16:19 โ€” ๐Ÿ‘ 2    ๐Ÿ” 0    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0
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Third speaker from the 2nd session on Day2 is delivered by Prof. Mathias O. Senge from @tcddublin @TCD_Chemistry #ECMolS2025

03.06.2025 11:14 โ€” ๐Ÿ‘ 4    ๐Ÿ” 2    ๐Ÿ’ฌ 1    ๐Ÿ“Œ 0
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TUM to receive funding for seven Clusters of Excellence In future, seven Clusters of Excellence at TUM and its cooperation partners will be funded.

Our university receives funding by the
@dfg.de for four renewed and three newly approved #ClustersofExcellence!๐Ÿ‘Research areas include #energy, #quantumtech, #health, and #societaltransformation. Congrats to all researchers involved! go.tum.de/844846 ๐ŸŽ‰

@wissenschaftsrat.de
๐Ÿ“ท @prolehre.bsky.social

22.05.2025 15:52 โ€” ๐Ÿ‘ 11    ๐Ÿ” 3    ๐Ÿ’ฌ 1    ๐Ÿ“Œ 1

Many thanks ๐Ÿ˜€

14.05.2025 16:59 โ€” ๐Ÿ‘ 0    ๐Ÿ” 0    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0
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Collaborative study with #TKoczorowski @pums-poznan.bsky.social ๐Ÿ‡ต๐Ÿ‡ฑ #MAFilatov @TUDubChemBPharm
+our group @tcddublin.bsky.social ๐Ÿ‡ฎ๐Ÿ‡ช on the spectroelectrochemistry of meso-aryl BODIPY out in #JMolStruct sciencedirect.com/science/arti... ๐Ÿ˜€#DyeSicPhoto @researchireland.bsky.social @tbsi-tcd.bsky.social

13.05.2025 19:51 โ€” ๐Ÿ‘ 8    ๐Ÿ” 1    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 1
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and at the same time Sophie, Liam, Freya and Karolina were busy at the @rsc.org #OrganicChemistryIreland meeting in Belfast ๐Ÿ˜€. #porphyrins #atropisomers #bicyclopentane #flowchemistry โš—๏ธ ... @researchireland.ie

09.05.2025 15:02 โ€” ๐Ÿ‘ 3    ๐Ÿ” 0    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0

Congratulations, nice ๐Ÿ˜€๐Ÿ‘

08.05.2025 16:38 โ€” ๐Ÿ‘ 2    ๐Ÿ” 0    ๐Ÿ’ฌ 1    ๐Ÿ“Œ 0
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Meeting old and new friends at the Bรผrgenstock conference #SCS_BC25 ๐Ÿ‡จ๐Ÿ‡ญ @aklymchenko.bsky.social #DanielGryko @mathiassenge.bsky.social ShoubhikDas ๐Ÿ˜€. Great meeting and great science ๐Ÿงชโš—๏ธ@swisschemistry.bsky.social

07.05.2025 21:16 โ€” ๐Ÿ‘ 13    ๐Ÿ” 2    ๐Ÿ’ฌ 1    ๐Ÿ“Œ 0
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Scientists reel as turmoil roils National Science Foundation The National Science Foundation, a major government funder of basic science research, is being shaken up with over 1,000 grants already terminated and the White House looking to halve its budget

The National Science Foundation, a major government funder of basic science research, is being shaken up with over 1,000 grants already terminated and the White House looking to halve its budget.

02.05.2025 18:54 โ€” ๐Ÿ‘ 3257    ๐Ÿ” 1375    ๐Ÿ’ฌ 201    ๐Ÿ“Œ 136
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Scientists reel as turmoil roils National Science Foundation The National Science Foundation, a major government funder of basic science research, is being shaken up with over 1,000 grants already terminated and the White House looking to halve its budget

www.npr.org/2025/05/02/n...

02.05.2025 18:59 โ€” ๐Ÿ‘ 2    ๐Ÿ” 1    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0

๐Ÿ˜

24.04.2025 14:59 โ€” ๐Ÿ‘ 3    ๐Ÿ” 0    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0
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Happy to welcome #JeanneIffrig who joins our group @tcddublin.bsky.social sky.social @tbsi-tcd.bsky.social
as an @euerasmusplus.bsky.social visiting researcher from @univ-amu.fr ๐Ÿ‡ซ๐Ÿ‡ท She is working on new types of #crownether containing sp3-rich rigid hydrocarbon unitsโš—๏ธ

24.04.2025 13:29 โ€” ๐Ÿ‘ 3    ๐Ÿ” 0    ๐Ÿ’ฌ 1    ๐Ÿ“Œ 0
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This study demonstrates a visible-light-induced topochemical #cycloaddition of a bimane derivative.ย 
โžก๏ธ https://www.beilstein-journals.org/bjoc/articles/21/37?B=yย 
#bimanes #cycloaddition #cyclobutanes. #fluorescence #BJOC ๐Ÿ’Ž๐Ÿ”“
@mathiassenge.bsky.social

22.04.2025 08:03 โ€” ๐Ÿ‘ 4    ๐Ÿ” 1    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0
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Nice group outing seeing the #bogskin exhibition ๐Ÿ–ผ๏ธ๐ŸŽจ@rha-arts.bsky.social and visiting with our artist friend #SiobhanMcDonal www.siobhanmcdonald.com
๐Ÿ˜€Great to see that #ArtScience is alive and flourishing!

14.04.2025 16:00 โ€” ๐Ÿ‘ 3    ๐Ÿ” 0    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0
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Very happy to welcome #ChiaraBaldi from #RobertaSessoli's group U Firenze ๐Ÿ‡ฎ๐Ÿ‡น as a visiting #PhD student in @tcddublin.bsky.social๐Ÿ˜€. Chiara will work with us on the synthesis of paramagnetic #porphyrins for optical and #chirality-induced #spin polarization โš—๏ธ@researchireland.bsky.social

07.04.2025 14:44 โ€” ๐Ÿ‘ 5    ๐Ÿ” 0    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0
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Exploring cage bicyclic hydrocarbons as bioisosteres for novel fragrances
www.chemistryviews.org/exploring-ne...

02.04.2025 00:55 โ€” ๐Ÿ‘ 1    ๐Ÿ” 1    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0

Many thanks Jose!

30.03.2025 05:25 โ€” ๐Ÿ‘ 1    ๐Ÿ” 0    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0

Thanks Fabienne ๐Ÿ˜€!

29.03.2025 16:53 โ€” ๐Ÿ‘ 1    ๐Ÿ” 0    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0

Great news for us in chemistry @tcddublin.bsky.social getting 2.6 Mioโ‚ฌ from @researchireland.bsky.social for new #NMR instrumentation ๐Ÿฅณ๐Ÿ“ข. This is critical for our research and teaching mission โš—๏ธ๐Ÿงช. Many thanks to #DonalOShea @rcsi-research.bsky.social and our experimental officers for their support!

29.03.2025 15:25 โ€” ๐Ÿ‘ 11    ๐Ÿ” 2    ๐Ÿ’ฌ 2    ๐Ÿ“Œ 0
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Free PDF of Condensed Version of IUPAC's Green Book - ChemistryViews Free PDF of Condensed Version of IUPAC's Green Book:

IUPACโ€™s official guide on quantities, units, and symbols (Green Book โ€“ abridged version) is available as a free PDF
www.chemistryviews.org/free-pdf-of-...

28.03.2025 09:15 โ€” ๐Ÿ‘ 4    ๐Ÿ” 4    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0
A bright study space with wooden walls, where four people sit around a table, engaged in discussion. In the background, others work or walk through the sunlit room.

A bright study space with wooden walls, where four people sit around a table, engaged in discussion. In the background, others work or walk through the sunlit room.

The TUM Global #Postdoc #Fellowship 2025 offers up to 10 international #youngscientists the opportunity to conduct research with a host at our #university for up to 2 years. Apply by April 13: go.tum.de/764681

#internationalization

๐Ÿ“ทA.Heddergott

25.03.2025 15:29 โ€” ๐Ÿ‘ 3    ๐Ÿ” 4    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0
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Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye Beilstein Journal of Organic Chemistry

Hehe, yes, no #porphyrin involved. If you look at this one www.beilstein-journals.org/bjoc/article... also no porphyrin ๐Ÿ˜œ. But never fear, we still do red and green chemistry๐Ÿ˜

18.03.2025 17:11 โ€” ๐Ÿ‘ 0    ๐Ÿ” 0    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0
A direct headspace injection method is presented and optimized for the analysis of volatile organic compounds (VOCs) using dielectric barrier discharge ionization-mass spectrometry (DBDI-MS), incorporating an intermediate vial in which the sample headspace is injected. The setup is built of commonly available, cheap consumable parts and easily enables the incorporation of different gases for generating different ionization atmospheres. The method can be fully automated by using standard GC autosamplers, and its rapid analysis time is suitable for high-throughput applications. We show that this method is suitable for both profiling analysis of complex samples such as biofluids and quantitative measurements for real-time reaction monitoring. Our optimized method demonstrated improved reproducibility and sensitivity, with detection limits for compounds tested in the high nanomolar to the low micromolar range, depending on the compound. Key parameters for method optimization were identified such as sample vial volume, headspace-to-liquid ratio, incubation temperature, and equilibration time. These settings were systematically evaluated to maximize the signal intensity and improve repeatability between measurements. Two use cases are demonstrated: (i) quantitative measurement of ethanol production by a metalโ€“organic framework from CO2 and (ii) profiling of biofluids following the consumption of asparagus.

A direct headspace injection method is presented and optimized for the analysis of volatile organic compounds (VOCs) using dielectric barrier discharge ionization-mass spectrometry (DBDI-MS), incorporating an intermediate vial in which the sample headspace is injected. The setup is built of commonly available, cheap consumable parts and easily enables the incorporation of different gases for generating different ionization atmospheres. The method can be fully automated by using standard GC autosamplers, and its rapid analysis time is suitable for high-throughput applications. We show that this method is suitable for both profiling analysis of complex samples such as biofluids and quantitative measurements for real-time reaction monitoring. Our optimized method demonstrated improved reproducibility and sensitivity, with detection limits for compounds tested in the high nanomolar to the low micromolar range, depending on the compound. Key parameters for method optimization were identified such as sample vial volume, headspace-to-liquid ratio, incubation temperature, and equilibration time. These settings were systematically evaluated to maximize the signal intensity and improve repeatability between measurements. Two use cases are demonstrated: (i) quantitative measurement of ethanol production by a metalโ€“organic framework from CO2 and (ii) profiling of biofluids following the consumption of asparagus.

Great to see this collaboration with #nicoleStrittmatter @tum.de ๐Ÿ‡ฉ๐Ÿ‡ช #AlinaMeindl ๐Ÿ‡ฆ๐Ÿ‡น @tcddublin.bsky.social
๐Ÿ‡ฎ๐Ÿ‡ช on 'Profiling of #VolatileOrganicCompounds' out in #JAmSocMassSpectrom @asms.org
pubs.acs.org/action/showC... ๐Ÿ˜€funded by @ias-tum.bsky.social
@researchireland.bsky.social

17.03.2025 18:29 โ€” ๐Ÿ‘ 5    ๐Ÿ” 1    ๐Ÿ’ฌ 1    ๐Ÿ“Œ 0
Bimanes, a class of molecules based on the 1H,7H-pyrazolo[1,2-a]pyrazole-1,7-dione scaffold, were first introduced by E. M. Kosower in 1978. In this study, we report the topochemical cycloaddition of diethyl 2,6-dichloro-1,7-dioxo-1H,7H-pyrazolo[1,2-a]pyrazole-3,5-dicarboxylate (Cl2B), initiated by visible light. Crystal structure analysis confirmed that the reactive double bonds are parallel and coplanar, in line with the Schmidt criteria for topochemical cycloaddition. Additionally, two other bimane derivatives with different substitution patterns were synthesized and investigated. Our findings suggest that functionalizing bimanes to redshift their absorption maxima into the visible-light spectrum provides a promising strategy for synthesizing substituted cyclobutanes without the need for ultraviolet irradiation.

Bimanes, a class of molecules based on the 1H,7H-pyrazolo[1,2-a]pyrazole-1,7-dione scaffold, were first introduced by E. M. Kosower in 1978. In this study, we report the topochemical cycloaddition of diethyl 2,6-dichloro-1,7-dioxo-1H,7H-pyrazolo[1,2-a]pyrazole-3,5-dicarboxylate (Cl2B), initiated by visible light. Crystal structure analysis confirmed that the reactive double bonds are parallel and coplanar, in line with the Schmidt criteria for topochemical cycloaddition. Additionally, two other bimane derivatives with different substitution patterns were synthesized and investigated. Our findings suggest that functionalizing bimanes to redshift their absorption maxima into the visible-light spectrum provides a promising strategy for synthesizing substituted cyclobutanes without the need for ultraviolet irradiation.

New paper out in #BJOC @beilstein-institut.bsky.social
Solid state #photochemistry for a change๐Ÿ˜‰โš—๏ธ"Visible light-initiated topochemical [2+2] cycloaddition in a #bimane dye" great collaboration with #MikhailFilatov @TUDubChemBPharm
funded by @researchireland.bsky.social doi.org/10.3762/bjoc...

05.03.2025 20:34 โ€” ๐Ÿ‘ 8    ๐Ÿ” 4    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0
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The annual @gdch.bsky.social
highlights in #OrganicChemistry โš—๏ธare out in #NachrichtenAusDerChemie ๐Ÿ“ข๐Ÿ˜€: doi.org/10.1002/nadc... again coordinated by @breugstlab.bsky.social

03.03.2025 15:14 โ€” ๐Ÿ‘ 4    ๐Ÿ” 0    ๐Ÿ’ฌ 0    ๐Ÿ“Œ 0

@mathiassenge is following 20 prominent accounts