Organic   Chemistry	Synthesis of enantiomerically pure macrocyclic oligo-malonates. Synthesis of C3-symmetric tripodal molecules. One-pot thermally chemocontrolled double Diels-Alder reactions.
Fullerene   Chemistry	Regioselective synthesis of multi-adducts of [60]fullerene via the tether-directed remote functionalization method. Synthesis and characterization of enantiomerically pure bis- and trisadducts of C60 with inherently chiral addition patterns. Synthesis of chiral hexakis adducts of C60 and dumbbell shaped bis(fullerene) amphiphiles. Azafullerene Chemistry.
Supramolecular   Chemistry	Study of enantiomerically pure trisadducts of C60 with an inherently chiral addition pattern in chiral photosensitization. Helically chiral fullerene coordination polymers. Construction of C60-containing molecular capsules consisted of calixarenes. Synthesis of carbonaceous materials with well-defined 3D-structures consisted of fullerene building units (Platonic solids, COFs). Study of amphiphilic fullerene derivatives in the formation of vesicles.

1. G. Vassilikogiannakis, N. Chronakis, and M. Orfanopoulos*, "A New [2+2] Functionalization of C₆₀ with Alkyl-Substituted 1,3-Butadienes: A Mechanistic Approach. Stereochemistry and Isotope Effects", J. Am. Chem. Soc., 1998, 120, 9911-9920.

 

2. N. Chronakis and M. Orfanopoulos*, "Ene Reaction of Arylallyl Alkenes with C₆₀. A Mechanistic Approach", Org. Lett., 1999, 1, 1909-1912.

 

3. N. Chronakis and M. Orfanopoulos*, "[4+2] Cycloadditions of Rigid s-cis Dienes to C₆₀. A Synchronous Diels-Alder Reaction", Org. Lett., 2001, 3, 545-548.

4. N. Chronakis and M. Orfanopoulos*, "Concerted Diels-Alder reaction between anthracene and C₆₀", Tetrahedron Lett., 2001, 42, 1201-1204.

5. N. Chronakis, G. C. Vougioukalakis, and M. Orfanopoulos*, "Synthesis and Self Photooxygenation of Alkenyl-Linked [60]Fullerene Derivatives. A Regioselective Ene Reaction", Org. Lett., 2002, 4, 945-948.

6. N. Chronakis, G. Froudakis, and M. Orfanopoulos*, "Stereochemistry of the [4+2] Cycloadditions of trans,trans and cis,trans-2,4-Hexadiene to C₆₀", J. Org. Chem., 2002, 67, 3284-3289.

7. G. C. Vougioukalakis, N. Chronakis, and M. Orfanopoulos*, "Addition of Electron-Rich Aromatics to Azafullereniun Carbocation. A Stepwise Electrophilic Substitution Mechanism", Org. Lett., 2003, 5, 4603-4606.

8. N. Chronakis and A. Hirsch*, "Regio- and stereoselective synthesis of enantiomerically pure [60]fullerene tris-adducts with an inherently chiral e,e,e addition pattern", Chem. Commun., 2005, 3709-3711.

9. F. Beuerle, N. Chronakis and A. Hirsch*, "Regioselective synthesis and zone selective deprotection of [60]fullerene tris-adducts with an e,e,e addition pattern", Chem. Commun., 2005, 3676-3678.

10. N. Chronakis*, A. Hirsch*, "Macrocyclic malonates. A new family of tethers for the regio- and diastereoselective functionalization of [60]fullerene", C. R. Chimie, 2006, 9, 862-867. (Review)

11. N. Chronakis, T. Brandmüller, C. Kovacs, U. Reuther, W. Donaubauer, F. Hampel, F. Fischer, F. Diederich*, and A. Hirsch*, "Macrocyclic Cyclo[n]Malonates - Synthetic Aspects and Observation of Columnar Arrangements by X-Ray Crystallography", Eur. J. Org. Chem., 2006, 2296-2308.

12. S. G. Kotsiris, Y. V. Vasil´ev, A. V. Streletskii, M. Han, L. P. Mark, O. V. Boltalina, N. Chronakis, M. Orfanopoulos, H. Hungerbühler and T. Drewello*, "Application and evaluation of solvent-free matrix-assisted laser desorption/ionization massspectrometry for the analysis of derivatized fullerenes", Eur. J. Mass Spectrom., 2006, 12, 397-408.

13. N. Chronakis*, U. Hartnagel. M. Braun and A. Hirsch*, "A chiral dumbbell shaped bis(fullerene) oligoelectrolyte", Chem. Commun., 2007, 607-609.

14. P. Witte, F. Beuerle, U. Hartnagel, R. Lebovitz, A. Savouchkina, S. Sali, D. Guldi*, N. Chronakis and A. Hirsch*, "Water solubility, antioxidant activity and cytochrome C binding of four families of exohedral adducts of C₆₀ and C₇₀", Org. Biomol. Chem., 2007, 5, 3599-3613.

15. S. Durdagi*, T. Mavromoustakos, N. Chronakis, M. G. Papadopoulos*, "Computational design of novel fullerene analogues as potential HIV-1 PR inhibitors: Analysis of the binding interactions between fullerene inhibitors and HIV-1 PR residues using 3D QSAR, molecular docking and molecular dynamics simulations", Bioorg. Med. Chem., 2008, 16, 9957-9974.

16. M. Riala and N. Chronakis*, "A Facile Access to Enantiomerically Pure [60]Fullerene Bisadducts with the Inherently Chiral Trans-3 Addition Pattern", Org. Lett., 2011, 13, 2844-2847.

17. M. Riala, M. S. Markoulides, E. E. Moushi and N. Chronakis*, "One-pot regioselective synthesis and X-ray crystal structure of a stable [60]fullerene trisadduct with the e_edge,e_face,trans-1 addition pattern", Chem. Commun., 2011, 47, 11948-11950.

18. M. J. Manos, M. S. Markoulides, C. D. Malliakas, G. S. Papaefstathiou, N. Chronakis, M. G. Kanatzidis, P. N. Trikalitis*, and A. J. Tasiopoulos*, "A Highly Porous Interpenetrated Metal-Organic Framework from the Use of a Novel Nanosized Organic Linker", Inorg. Chem., 2011, 50, 11297-11299.

19. M. S. Markoulides, C. P. Ioannou, M. J. Manos and N. Chronakis*, "Quantitative preparation of 3,4-di(methylene tetrahydrothiophene-1,1-dioxide by Zn-induced 1,4-debromination. A valuable 6-C reactive diene in [4+2] cycloadditions with DMAD and [60]fullerene", RSC Adv., 2012, 2, 12269-12277.

20. M. S. Markoulides, G. I. Ioannou, M. J. Manos and N. Chronakis*, "One-pot thermally chemocontrolled double Diels-Alder strategies. A route to [4+2] functionalisation/[4+2] derivatization of C₆₀", RSC Adv., 2013, 3, 4750-4756.

21. M. Riala and N. Chronakis*, "Remote Functionalization of C₆₀ with Enantiomerically Pure cyclo-[2]-Malonate Tethers Bearing C12 and C14 Spacers: Synthetic Access to Bisadducts of C₆₀ with the Inherently Chiral trans-3 Addition Pattern", J. Org. Chem., 2013, 78, 7701-7713. (Highlighted paper)

22. C. P. Ioannou and N. Chronakis*, "The first one-pot synthesis of a chiral pentakis-adduct of C₆₀ utilising an opened-structure malonate tether", Chem. Commun., 2013, 49, 10611-10613.

23. M. Riala and N. Chronakis*, "An unexpected stereoisomerism in enantiomerically pure trisadducts of C₆₀ with an inherently chiral trans-3,trans-3,trans-3 addition pattern", Chem. Commun., 2014, 50, 1995-1998.

24. N. Chronakis*, "The journey of L-tartaric acid in the world of enantiomerically pure bis- and trisadducts of C₆₀ with the inherently chiral trans-3 and all-trans-3 addition patterns", Org. Biomol. Chem., 2014, 12, 8574-8579. (Invited Perspective)

25. C. P. Ioannou and N. Chronakis*, "A study towards the regioselective synthesis of the e,e,e trisadduct of C₆₀ via the [4+2] Diels-Alder reaction with tethers bearing ortho-quinodimethane precursors", Arkivoc, 2015, 65-82. (Commemorative issue dedicated to Professor Michael Orfanopoulos on the occasion of his 67^th birthday)

26. C. P. Ioannou, G. I. Ioannou, E. E. Moushi, K. Velonia* and N. Chronakis*, "Self-Assembled Giant Vesicles Formed by Type I [3:3]-Hexakis Adducts of C₆₀ Equipped with Enantiomerically Pure cyclo-Monomalonate Addends", Eur. J. Org. Chem., 2015, 4598-4602.

27. M. S. Markoulides*, C. G. Efthymiou, A. J. Tasiopoulos, N. Chronakis*, "Design and synthesis of new nanosized C₃-symmetrical tricarboxylic acids: key elongated ligands for the preparation of highly porous MOFs", Synlett, 2015, 26, 2659-2662.

28. Birkett P.R., and Chronakis N., Fullerene Chemistry. In: Saleem Hashmi (editor-in-chief), Reference Module in Materials Science and Materials Engineering. Oxford: Elsevier; 2016. pp. 1-6. (Invited book chapter)

29. M. Riala, K. L. Maxouti, C. P. Ioannou, and N. Chronakis*, "Synthesis of Enantiopure T-Symmetrical [6:0]-Hexakis Adducts of C₆₀ Equipped with 1,2-Glycol Substituted cyclo-Monomalonate Addends", Org. Lett., 2016, 18, 1132-1135.

30. J.-Y. Yue, M. Markoulides, A. C. Regan, S.-Y. Li, N. Chronakis, A. Gourdon, T. Chen, H.-J. Yan, and D. Wang*, "Construction of 2D nanoporous network by coupling on-surface dynamic imine chemistry and dipole-stabilized self-assembly", Chem. Commun., 2017, 53, 428-431.

31. A. Stergiou, K. Asad, A. Kourtellaris, N. Chronakis*, N. Tagmatarchis*, "Tether-directed Regioselective Synthesis of an Equatorial_face Bisadduct of Azafullerene Using Cyclo-[2]-octylmalonate", Chem. Eur. J., 2019, 25, 5751-5756.

32. C. García-Simón, C. Colomban, Y. Aybars Çetin, A. Gimeno, M. Pujals, E. Ubasart, C. Fuertes-Espinosa, K. Asad, N. Chronakis, M. Costas, J. Jiménez-Barbero*, F. Feixas*, X. Ribas*, "Complete Dynamic Reconstruction of C₆₀, C₇₀ and (C₅₉N)₂ Encapsulation into an Adaptable Supramolecular Nanocapsule", J. Am. Chem. Soc., 2020, 142, 16051-16063.

33. A. Kourtellaris, M. S. Markoulides, N. Chronakis, S. J. Teat, J. C. Plakatouras, and A. J. Tasiopoulos*, "Isoreticular Design of Two Novel Metal Organic Frameworks and Their Single-Crystal-to-Single-Crystal Solvent Exchange Properties", Cryst. Growth Des., 2020, 20, 7822-7832.

34. E. Ubasart, C. García-Simón, M. Pujals, K. Asad, N. Chronakis, Teodor Parella, Xavi Ribas*, "Straightforward supramolecular purification of C₈₄ from fullerene extract", Org. Chem. Front., 2021, 8, 4101-4105.

35. K. Asad, A. Stergiou, A. Kourtellaris, N. Tagmatarchis*, N. Chronakis*, "First Synthesis of the Inherently Chiral Trans-4' Bisadduct of C₅₉N Azafullerene by Using Cyclo-[2]-dodecylmalonate as a Tether", Chem. Eur. J., 2021, 27, 13879-13886. (HOT PAPER, Invited paper for the Joint Special Collection dedicated to François Diederich)

 

Patents

1. Andreas Hirsch, Florian Beuerle, and Nikos Chronakis, "Method of Synthesis of Water Soluble Fullerene Polyacids Using a Malonate Reactant" U.S. PATENT No2006/047167.