SNF Ambizione Fellow


Dr. Michal Juríček




University of Basel
Department of Chemistry
St.Johannsring 19
CH-4056 Basel

E-mail:michal.juricek@unibas.ch

Phone: +41 (0)61 2071015

Office: AC210
Lab: OC04




Research | Education | Publications | CV | People









Research




Graphene fragments made of exclusively carbon and hydrogen atoms are useful molecular models, which aid and abet our understanding of intrinsic phenomena occurring in graphene. The well-defined structure of these fragments allows us to investigate how the desired properties relate to the structure on a small scale first, before moving to extended two-dimensional carbon networks. Chemistry of graphene fragments is well documented in the literature, with the exception of one class of these hydrocarbon molecules, namely, the “open-shell graphene fragments”. Their unique triangular topology breaks the “alternating-double-bond rule” (see the figure below) and, as a result, these molecules contain unpaired delocalized electrons. In general, an increase of the fragment size leads to a higher number of unpaired electrons. The main reason for which the open-shell graphene fragments have not been studied to a great extent is the extremely low stability of systems containing unpaired electrons, the so-called free radicals. The majority of reports on open-shell graphene fragments describe derivatives of the smallest fragment, monoradical phenalenyl (1, three fused benzene rings), and only a few examples mention its larger homolog, diradical triangulene (2, six fused benzene rings). In fact, only one derivative of triangulene composed of only carbon and hydrogen atoms has been described so far, however, it could only detected under strictly inert conditions and at low temperatures because of its instability. The goal of our research is to synthesize and characterize, both in solution and in the solid phase, a persistent derivative of triangulene, and theoretically and experimentally validate its triplet ground state. The unpaired electrons in triangulene and its larger homologs (such as 3) can, in principle, serve as information carriers and potentially be used in the design of quantum information processing devices.




Students interested in working on this project are very welcome (please send an email to michal.juricek@unibas.ch).





Education





2011 – PhD in Science
Radboud University Nijmegen (The Netherlands)
Advisor: Professor Alan E Rowan
Doctoral thesis on Triazole Materials: Towards Extending Aromaticity
http://repository.ubn.ru.nl/bitstream/handle/2066/90911/90911.pdf?sequence=1
 
2005 – MSc (Hons) in Organic Chemistry
Comenius University in Bratislava (Slovakia)
Advisor: Associate Professor Martin Putala
Master’s thesis on Novel Chiral Binaphthyls for Non-Linear Optics
 
2003 – BSc in Organic Chemistry
Comenius University in Bratislava (Slovakia)
 

I was born in Bojnice and grew up in Prievidza, both small towns in Slovakia. I received my PhD Degree from Radboud University Nijmegen in The Netherlands in the group of Professor Alan Rowan, where I investigated triazole-derived materials and methods to extend aromaticity. In the Stoddart group, I worked as a Postdoctoral Scholar on molecular flash memory devices (Rubicon Fellowship from NWO) and extended viologen cyclophanes – ExBox. Currently I conduct an independent research (SNF Ambizione Fellowship) hosted by Professor Marcel Mayor at the University of Basel in Switzerland, aiming to experimentally and theoretically validate the multiplet ground state of open-shell graphene fragments.
 
http://scholar.google.ch/citations?user=A0iacEUAAAAJ&hl=en






Publications




Independent Research

[22] P. Ravat, T. Šolomek, M. Rickhaus, D. Häussinger, M. Neuburger, M. Baumgarten and M. Juríček, “Cethrene: A helically chiral biradicaloid isomer of heptazethrene” Angew. Chem. Int. Ed. 2015, Early View, DOI: 10.1002/anie.201507961.

http://onlinelibrary.wiley.com/doi/10.1002/anie.201507961/abstract

 


With J Fraser Stoddart

[21] J. C. Barnes, E. J. Dale, A. Prokofjevs, A. Narayanan, I. C. Gibbs-Hall, M. Juríček, C. L. Stern, A. A. Sarjeant, Y. Y. Botros, S. I. Stupp and J. F. Stoddart, “Semiconducting single crystals comprising segregated arrays of complexes of C60 J. Am. Chem. Soc. 2015, 137, 2392–2399.

http://pubs.acs.org/doi/abs/10.1021/ja512959g




 

[20] E. J. Dale, N. A. Vermeulen, A. A. Thomas, J. C. Barnes, M. Juríček, A. K. Blackburn, N. L. Strutt, A. A. Sarjeant, C. L. Stern, S. E. Denmark and J. F. Stoddart, “ExCage” J. Am. Chem. Soc. 2014, 136, 10669–10682.
 
http://pubs.acs.org/doi/abs/10.1021/ja5041557

 


[19] M. Juríček, J. C. Barnes, N. L. Strutt, N. A. Vermeulen, K. C. Ghooray, E. J. Dale, P. R. McGonigal, A. K. Blackburn, A.-J. Avestro and J. F. Stoddart, “An ExBox [2]catenane” Chem. Sci. 2014, 5, 2724–2731.
 
http://pubs.rsc.org/en/Content/ArticleLanding/2014/SC/c4sc00488d#!divAbstract




[18] S. M. Dyar, J. C. Barnes, M. Juríček, J. F. Stoddart, D. T. Co, R. M. Young and M. R. Wasielewski, “Electron transfer and multi-electron accumulation in ExBox4+ Angew. Chem. Int. Ed. 2014, 53, 5371–5385.

http://onlinelibrary.wiley.com/doi/10.1002/anie.201402444/abstract



 

[17] M. Juríček, N. L. Strutt, J. C. Barnes, A. M. Butterfield, E. J. Dale, K. K. Baldridge, J. F. Stoddart and J. S. Siegel, “Induced-fit catalysis of corannulene bowl-to-bowl inversion” Nature Chem. 2014, 6, 222–228.
  • Featured in Nature Chemistry News and Views 2014, 6, 177–178 (February 20, 2014)
  • Featured in C&E News 2014, 92, 25 (January 27, 2014)
http://www.nature.com/nchem/journal/v6/n3/full/nchem.1842.html


 
[16] J. C. Barnes,† M. Juríček,† N. A. Vermeulen†, E. J. Dale and J. F. Stoddart, “Synthesis of ExnBox cyclophanes” J. Org. Chem. 2013, 78, 11962–11969.
  •  † Equal contributions
http://pubs.acs.org/doi/abs/10.1021/jo401993n


 
[15] R. M. Young, S. M. Dyar, J. C. Barnes, M. Juríček, J. F. Stoddart, D. T. Co and M. R. Wasielewski, “Ultrafast conformational dynamics of electron accumulation in ExBox4+ cyclophane” J. Phys. Chem. A 2013, 117, 12438–12448.
 
http://pubs.acs.org/doi/abs/10.1021/jp409883a

 
[14] M. Juríček,† J. C. Barnes,† E. J. Dale, W.-G. Liu, N. L. Strutt, C. J. Bruns, N. A. Vermeulen, K. C. Ghooray, A. A. Sarjeant, C. L. Stern, Y. Y. Botros, W. A. Goddard, III and J. F. Stoddart, “Ex2Box: Interdependent modes of binding in a two-nanometer-long synthetic receptor” J. Am. Chem. Soc. 2013, 135, 12736–12746.
  • † Equal contributions
 http://pubs.acs.org/doi/abs/10.1021/ja4052763

 
[13] D. Cao, M. Juríček, Z. J. Brown, A. C.-H. Sue, Z. Liu, J. Lei, A. K. Blackburn, S. Grunder, A. A. Sarjeant, A. Coskun, C. Wang, O. K. Farha, J. T. Hupp and J. F. Stoddart, “Three-dimensional architectures incorporating stereoregular donor–acceptor stacks” Chem.–Eur. J. 2013, 19, 8457–8465.
 
http://onlinelibrary.wiley.com/doi/10.1002/chem.201300762/full

 
[12] J. C. Barnes,† M. Juríček,† N. L. Strutt, M. Frasconi, S. Sampath, M. A. Giesener, P. L. McGrier, J. C. Bruns, C. L. Stern, A. A. Sarjeant and J. F. Stoddart, “ExBox: A polycyclic aromatic hydrocarbon scavenger” J. Am. Chem. Soc. 2013, 135, 183–192.
  • † Equal contributions
  • Cover Article
  • Featured in JACS Spotlights: November 13, 2012 
  • Featured in Chemistry World: October 15, 2012
  • Featured in C&E News: September 12, 2012
 http://pubs.acs.org/doi/abs/10.1021/ja307360n

 

With Alan E Rowan

 
[11] F. J. van den Bruele, W. de Poel, H. W. M. Sturmans, S. Pintea, R. de Gelder, D. Wermeille, M. Juríček, A. E. Rowan, W. J. P. van Enckevort and E. Vlieg, “Monolayer and aggregate formation of a modified phthalocyanine on mica determined by a delicate balance of surface interactions” Surf. Sci. 2012, 606, 830–835.
 
http://www.sciencedirect.com/science/article/pii/S0039602812000350

 
[10] M. Juríček, K. Stout, P. H. J. Kouwer and A. E. Rowan, “The trisubstituted-triazole approach to extended functional naphthalocyanines” J. Porphyrins Phthalocyanines 2011, 15, 898–907. 
  • Invited article in honor of Professor Karl M Kadish
http://www.worldscientific.com/doi/abs/10.1142/s1088424611003781
 
 
[9] M. Juríček, K. Stout, P. H. J. Kouwer and A. E. Rowan, “Fusing triazoles: Toward extending aromaticity” Org. Lett. 2011, 13, 3494–3497.
  • Featured in Synfacts 2011, 9, 0958–0958
http://pubs.acs.org/doi/abs/10.1021/ol201290q

 
[8] M. Juríček, P. H. J. Kouwer and A. E. Rowan, “Triazole: A unique building block for the construction of functional materials” Chem. Commun. 2011, 47, 8740–8749.
  • Invited Chemical Communications Feature Article
http://pubs.rsc.org/en/content/articlehtml/2011/cc/c1cc10685f
 
 
[7] M. Juríček, M. Felici, P. Contreras-Carballada, J. Lauko, S. Rodríguez Bou, P. H. J. Kouwer, A. M. Brouwer and A. E. Rowan, “Triazole–pyridine ligands: A novel approach to chromophoric iridium arrays” J. Mater. Chem. 2011, 21, 2104–2111.
  • Selected by editor as Hot Article: December 21, 2010
http://pubs.rsc.org/en/content/articlehtml/2011/jm/c0jm03117h

 
[6] S. Albert-Seifried, C. E. Finlayson, F. Laquai, R. H. Friend, T. M. Swager, P. H. J. Kouwer, M. Juríček, H. J. Kitto, S. Valster, R. J. M. Nolte and A. E. Rowan, “Multichromophoric phthalocyanine–perylenediimide “octads”: A photophysical study”
Chem.–Eur. J. 2010, 16, 10021–10029.
 
http://onlinelibrary.wiley.com/doi/10.1002/chem.201000677/full
 
 
[5] M. Juríček, P. H. J. Kouwer, J. Rehák, J. Sly and A. E. Rowan, “A novel modular approach to triazole-functionalized phthalocyanines using click chemistry” J. Org. Chem. 2009, 74, 21–25.
  • Selected by journal to be published as The Journal of Organic Chemistry Featured Article
http://pubs.acs.org/doi/abs/10.1021/jo802078f

 

With Martin Putala

 
[4] M. Juríček, P. Kasák, M. Stach and M. Putala, “Potential 1,1’-binaphthyl NLO-phores with extended conjugation between positions 2 and 6, and 2’ and 6’” Tetrahedron Lett. 2007, 48, 8869–8873.
 
http://www.sciencedirect.com/science/article/pii/S0040403907020412
 
[3] M. Juríček, H. Brath, P. Kasák and M. Putala, “Study on the electronic effects on stereoconservativity of Suzuki coupling in chiral groove of binaphthyl” J. Organomet. Chem. 2007, 692, 5279–5284.
 
http://www.sciencedirect.com/science/article/pii/S0022328X07005888
 
[2] H. Brath, M. Dubovská, M. Juríček, P. Kasák and M. Putala, “Novel route to enantiopure 2,2’-diaryl-1,1’-binaphthalenes by stereoconservative Suzuki arylation at positions 2 and 2’” Collect. Czech. Chem. Commun. 2004, 69, 1517–1536.
 
http://cccc.uochb.cas.cz/69/7/1517/
 
[1] P. Kasák, H. Brath, M. Dubovská, M. Juríček and M. Putala, “Suzuki arylation at positions 2 and 2’ of 1,1’-binaphthyls: Stereochemical result depending on the sense of polarity of substrates” Tetrahedron Lett. 2004, 45, 791–794.
 
http://www.sciencedirect.com/science/article/pii/S0040403903027278
 

Patents

  
[2] J. F. Stoddart, E. J. Dale, N. A. Vermeulen, J. C. Barnes and M. Juríček, “ExCage: Synthesis of viologen-like pyridinium-based cages for the selective capture of polycyclic aromatic hydrocarbons” US Utility Patent Application No. or PCT International Application Serial No. 14/844’577.

[1] J. F. Stoddart, J. C. Barnes and M. Juríček, “Tetracationic cyclophanes and their use in the sequestration of polyaromatic hydrocarbons by way of complexation” US Utility Patent Application No. 14/136,870, Filing Date December 20, 2013 and PCT International Application Serial No. PCT/US2013/077144, Filing Date December 20, 2013.