Christos P. Constantinides

Publications

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From the University of Michigan – Dearborn

  1. Constantinides, C. P.; Yi, J.-S.; Marincean, S. Solid-state structure and supramolecular packing of 1,2-bis(2-phenyl-1H-benzo[d]imidazol-1-yl)diazene. Acta Crystallogr., Sect. E:Crystallogr. Commun. 2026, 82 (6), 717–721. DOI: 10.1107/S2056989026005098.
  2. Constantinides, C. P.; Yi, J.-S.; Dakdouk, H.; Marincean, S. Positional Methyl Effects in Benzo[e][1,2,4]triazines—Synthesis and Crystal Structure Analysis of 5-Methyl-3-phenylbenzo[e][1,2,4]triazine and Its Precursor, N′-(3-Methyl-2-nitrophenyl)benzohydrazide. Crystals 2026, 16 (3), 206. DOI: 10.3390/cryst16030206.
  3. Hernández, A.; Zissimou, G. A.; Ortiz, J.; Kourtellaris, A.; Constantinides, C. P.; Lawson, D. B.; Hu, Z.; Coronado, E.; Koutentis, P. A.; Sastre-Santos, Á. Unsymmetrical β-Fused Blatter Radical Zinc Phthalocyanines. Chem. Eur. J. 2026, 32 (4), e03294. DOI: 10.1002/chem.202503294.
  4. Constantinides, C. P.; Raza, S.; Bazzi, F.; Sharara, N.; Marincean, S. Comparative Analysis of the Substituent Effects on the Supramolecular Structure of N′-(4-Methyl-2-nitrophenyl)benzohydrazide and N′-(2-Nitro-(4-trifluoromethyl)phenyl)benzohydrazide. Crystals 2025, 15 (8), 732. DOI: 10.3390/cryst15080732.
  5. Constantinides, C. P.; Raza, S.; Bazzi, F.; Sharara, N.; Marincean, S. Synthesis and Crystal Structures of 6- and 8-Methyl-3-phenylbenzo[e][1,2,4]triazines. Acta Crystallogr., Sect. E:Crystallogr. Commun. 2025, 81 (8), 699–705. DOI: 10.1107/S2056989025005882.
  6. Southern, S. A.; Zissimou, G. A.; Flesariu, D. F.; Bazzi, F.; Nicolaides, C.; Trypiniotis, T.; Constantinides, C. P.; Koutentis, P. A.; Perras, F. A. In Silico Design of Methyl-Driven Overhauser Dynamic Nuclear Polarization Agents. J. Phys. Chem. Lett. 2025, 16, 6219–6225. DOI: 10.1021/acs.jpclett.5c01375.
  7. Constantinides, C. P.; Berezin, A. A.; Flores, G. E.; Early, B.; Zissimou, G. A.; Flesariu, D. F.; Lawson, D. B.; Manoli, M.; Leitus, G.; Koutentis, P. A. Ferromagnetic Interactions within a Dimer of a π-Extended 1,2,4-Benzotriazin-4-yl. Cryst. Growth Des. 2025, 25, 1164–1173. DOI: 10.1021/acs.cgd.4c01508.
  8. Chrysochos, N.; Constantinides, C. P.; Leitus, G. M.; Kourtellaris, A.; Lawson, D. B.; Deumal, M.; Ribas-Ariño, J.; Carvajal, M. À.; Zissimou, G. A.; Nicolaides, C.; Trypiniotis, T.; Koutentis, P. A. Temperature-Dependent Antiferromagnetic Exchange along 1D Linear Regular Chains of the Phthalonitrile Blatter Radical. Cryst. Growth Des. 2023, 23, 8939–8952. DOI: 10.1021/acs.cgd.3c00999.
  9. Nicolaides, C.; Bazzi, F.; Vouros, E.; Flesariu, D. F.; Chrysochos, N.; Koutentis, P. A.; Constantinides, C. P.; Trypiniotis, T. Metal-Free Organic Radical Spin Source. Nano Lett. 2023, 23, 4579–4586. DOI: 10.1021/acs.nanolett.3c01044.
  10. Obijalska, E.; Pietrzak, A.; Constantinides, C. P.; Sommer, R. D.; Kaszynski, P. Super stable Blatter radicals through ArLi additions: surprising chemistry of 7-(trifluoromethyl)benzo[e][1,2,4]triazine. Chem. Commun. 2023, 59, 4008–4011. DOI: 10.1039/D3CC00832K.
  11. Perras, F. A.; Matsuki, Y.; Southern, S. A.; Dubroca, T.; Flesariu, D. F.; Van Tol, J.; Constantinides, C. P.; Koutentis, P. A. Mechanistic origins of methyl-driven Overhauser DNP. J. Chem. Phys. 2023, 158, 154201. DOI: 10.1063/5.0149664.
  12. Boudalis, A. K.; Constantinides, C. P.; Chrysochos, N.; Carmieli, R.; Leitus, G.; Kourtellaris, A.; Lawson, D. B.; Koutentis, P. A. Deciphering the ground state of a C3-symmetrical Blatter-type triradical by CW and pulse EPR spectroscopy. J. Magn. Reson. 2023, 349, 107406. DOI: 10.1016/j.jmr.2023.107406.
  13. Broadhurst, E. T.; Wilson, C. J. G.; Zissimou, G. A.; Padrón Gómez, M. A.; Vasconcelos, A. M. L.; Constantinides, C. P.; Koutentis, P. A.; Ayala, A. P.; Parsons, S. The Effect of High Pressure on Polymorphs of a Derivative of Blatter’s Radical: Identification of the Structural Signatures of Subtle Phase Transitions. Cryst. Growth Des. 2023, 23, 1915–1924. DOI: 10.1021/acs.cgd.2c01422.
  14. Perras, F. A.; Flesariu, D. F.; Southern, S. A.; Nicolaides, C.; Bazak, J. D.; Washton, N. M.; Trypiniotis, T.; Constantinides, C. P.; Koutentis, P. A. Methyl-Driven Overhauser Dynamic Nuclear Polarization. J. Phys. Chem. Lett. 2022, 13, 4000–4006. DOI: 10.1021/acs.jpclett.2c00748.
  15. Broadhurst, E. T.; Wilson, C. J. G.; Zissimou, G. A.; Nudelman, F.; Constantinides, C. P.; Koutentis, P. A.; Parsons, S. A first-order phase transition in Blatter’s radical at high pressure. Acta Crystallogr., Sect. B:Struct. Sci., Cryst. Eng. Mater. 2022, 78, 107–116. DOI: 10.1107/S2052520622000191.
  16. Constantinides, C. P.; Koyioni, M.; Bazzi, F.; Manoli, M.; Lawson, D. B.; Koutentis, P. A. Crystal Structure and Solid-State Packing of 4-Chloro-5H-1,2,3-dithiazol-5-one and 4-Chloro-5H-1,2,3-dithiazole-5-thione. Molecules 2021, 26, 5875. DOI: 10.3390/molecules26195875.
  17. Constantinides, C. P.; Lawson, D. B.; Zissimou, G. A.; Berezin, A. A.; Mailman, A.; Manoli, M.; Kourtellaris, A.; Leitus, G. M.; Clérac, R.; Tuononen, H. M.; Koutentis, P. A. Polymorphism in a π-stacked Blatter radical: structures and magnetic properties of 3-(phenyl)-1-(pyrid-2-yl)-1,4-dihydrobenzo[e][1,2,4]triazine-4-yl. CrystEngComm 2020, 22, 5453–5463. DOI: 10.1039/D0CE00789G.
  18. Bazzi, F.; Danke, A. J.; Lawson, D. B.; Manoli, M.; Leitus, G. M.; Koutentis, P. A.; Constantinides, C. P. 1-(2-Methoxyphenyl)-3-phenyl-1,4-dihydro-1,2,4-benzotriazin-4-yl: a tricky “structure-to-magnetism” correlation aided by DFT calculations. CrystEngComm 2020, 22, 4306–4316. DOI: 10.1039/D0CE00669F.
  19. Constantinides, C. P.; Lawson, D. B.; Berezin, A. A.; Zissimou, G. A.; Manoli, M.; Leitus, G. M.; Koutentis, P. A. Ferromagnetic Interactions in a 1D Heisenberg Linear Chain of 1-Phenyl-3,7-bis(trifluoromethyl)-1,4-dihydro-1,2,4-benzotriazin-4-yls. CrystEngComm 2019, 21, 4599–4606. DOI: 10.1039/C9CE00739C.
  20. Beldjoudi, Y.; Nascimento, M. A.; Cho, Y. J.; Yu, H.; Aziz, H.; Tonouchi, D.; Eguchi, K.; Matsushita, M. M.; Awaga, K.; Osorio-Roman, I.; Constantinides, C. P.; Rawson, J. M. Multifunctional Dithiadiazolyl Radicals: Fluorescence, Electroluminescence, and Photoconducting Behavior in Pyren-1′-yl-dithiadiazolyl. J. Am. Chem. Soc. 2018, 140, 6260–6270. DOI: 10.1021/jacs.7b12592.

From Doctoral and Post-Doctoral studies

  1. Savva, A. C.; Mirallai, S. I.; Zissimou, G. A.; Berezin, A. A.; Demetriades, M.; Kourtellaris, A.; Constantinides, C. P.; Nicolaides, C.; Trypiniotis, T.; Koutentis, P. A. Preparation of Blatter Radicals via Aza-Wittig Chemistry: The Reaction of N-Aryliminophosphoranes with 1-(Het)aroyl-2-aryldiazenes. J. Org. Chem. 2017, 82, 7564–7575. DOI: 10.1021/acs.joc.7b01297.
  2. Constantinides, C. P.; Carter, E.; Eisler, D.; Beldjoudi, Y.; Murphy, D. M.; Rawson, J. M. Effects of Halo-substitution on 2'-Chloro-5'-halo-phenyl-1,2,3,5-dithiadiazolyl Radicals: A Crystallographic, Magnetic and EPR Case Study. Cryst. Growth Des. 2017, 17, 3017–3029. DOI: 10.1021/acs.cgd.6b01700.
  3. Karekla, G.; Papagiorgis, P.; Panayi, N.; Zissimou, G. A.; Constantinides, C. P.; Koutentis, P. A.; Itskos, G.; Hayes, S. C. Emission from the stable Blatter radical. New J. Chem. 2017, 41, 8604–8613. DOI: 10.1039/C7NJ00677B.
  4. Kaszynski, P.; Constantinides, C. P.; Young, V. G. The Planar Blatter Radical: A New Paradigm in the Structural Chemistry of 1,4-Dihydrobenzo[e][1,2,4]triazin-4-yl. Angew. Chem., Int. Ed. 2016, 55, 11149–11152. DOI: 10.1002/anie.201605612.
  5. Constantinides, C. P.; Berezin, A. A.; Zissimou, G. A.; Manoli, M.; Leitus, G. M.; Koutentis, P. A. The Suppression of Columnar π-Stacking in 3-Adamantyl-1-phenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl. Molecules 2016, 21 (5), 636. DOI: 10.3390/molecules21050636. (Invited paper for the special issue “Free Radicals in Organic Synthesis”).
  6. Constantinides, C. P.; Obijalska, E.; Kaszynski, P. Access to 1,4-Dihydrobenzo[e][1,2,4]triazin-4-yl Derivatives. Org. Lett. 2016, 18, 916–919. DOI: 10.1021/acs.orglett.5b03528.
  7. Zissimou, G. A.; Constantinides, C. P.; Manoli, M.; Pieridou, G. K.; Hayes, S. C.; Koutentis, P. A. Oxidation of Tetraphenylhexaazaathracene: Accessing a Scissor Dimer of a 16π Biscyanine. Org. Lett. 2016, 18, 1116–1119. DOI: 10.1021/acs.orglett.6b00222.
  8. Constantinides, C. P.; Zissimou, G. A.; Berezin, A. A.; Ioannou, T. A.; Manoli, M.; Tsokkou, D.; Theodorou, E.; Hayes, S. C.; Koutentis, P. A. Tetraphenylhexaazaanthracenes: 16π Weakly Antiaromatic Species with Singlet Ground States. Org. Lett. 2015, 17, 4026–4029. DOI: 10.1021/acs.orglett.5b01923. (Highlighted in SYNFACTS, September 18, 2015; Synfacts 2015, 11 (10), 1049.)
  9. Theodorou, E.; Ioannidou, H. A.; Ioannou, T. H.; Kalogirou, A. S.; Constantinides, C. P.; Manoli, M.; Koutentis, P. A.; Hayes, S. C. Spectroscopic Characterization of C-4 Substituted 3,5-Dichloro-4H-1,2,6-thiadiazines. RSC Adv. 2015, 5, 18471–18481. DOI: 10.1039/C4RA16144K.
  10. Constantinides, C. P.; Berezin, A. A.; Zissimou, G. A.; Manoli, M.; Leitus, G. M.; Bendikov, M.; Probert, M. R.; Rawson, J. M.; Koutentis, P. A. A Magnetostructural Investigation of an Abrupt Spin Transition for 1-Phenyl-3-trifluoromethyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl. J. Am. Chem. Soc. 2014, 136, 11906–11909. DOI: 10.1021/ja5063746. (Highlighted in JACS Spotlights, August 20, 2014).
  11. Constantinides, C. P.; Eisler, D. J.; Alberola, A.; Carter, E.; Murphy, D. M.; Rawson, J. M. Weakening of the π*–π* dimerisation in 1,2,3,5-dithiadiazolyl radicals: structural, EPR, magnetic and computational studies of dichlorophenyl dithiadiazolyls, Cl2C6H3CNSSN˙. CrystEngComm 2014, 16, 7298–7312. DOI: 10.1039/c4ce00308j. (Invited paper for the North American IYCr celebration issue; designated a hot article in May 2014 and invited to contribute front-cover artwork).
  12. Constantinides, C. P.; Berezin, A. A.; Manoli, M.; Leitus, G. M.; Zissimou, G. A.; Bendikov, M.; Rawson, J. M.; Koutentis, P. A. Structural, Magnetic and Computational Correlations of Some Imidazolo-Fused 1,2,4‑Benzotriazinyl Radicals. Chem. Eur. J. 2014, 20, 5388–5396. DOI: 10.1002/chem.201304538.
  13. Constantinides, C. P.; Berezin, A. A.; Manoli, M.; Leitus, G. M.; Bendikov, M.; Rawson, J. M.; Koutentis, P. A. Effective exchange coupling in alternating-chains of a π-extended 1,2,4-benzotriazin-4-yl. New J. Chem. 2014, 38, 949–954. DOI: 10.1039/C3NJ01235B.
  14. Berezin, A. A.; Zissimou, G.; Constantinides, C. P.; Beldjoudi, Y.; Rawson, J. M.; Koutentis, P. A. Route to Benzo- and Pyrido-Fused 1,2,4-Triazinyl Radicals via N'-(Het)aryl-N'-[2-nitro(het)aryl]hydrazides. J. Org. Chem. 2014, 79, 314–327. DOI: 10.1021/jo402481t.
  15. Berezin, A. A.; Constantinides, C. P.; Mirallai, S. I.; Manoli, M.; Cao, L. L.; Rawson, J. M.; Koutentis, P. A. Synthesis and properties of imidazolo-fused benzotriazinyl radicals. Org. Biomol. Chem. 2013, 11, 6780–6795. DOI: 10.1039/c3ob41169a.
  16. Constantinides, C. P.; Carter, E.; Murphy, D. M.; Manoli, M.; Leitus, G. M.; Bendikov, M.; Rawson, J. M.; Koutentis, P. A. Spin-triplet excitons in 1,3-diphenyl-7-(fur-2-yl)-1,4-dihydro-1,2,4-benzotriazin-4-yl. Chem. Commun. 2013, 49, 8662–8664. DOI: 10.1039/c3cc44899a.
  17. Kasiouli, S.; DiStasio, F.; McDonnell, S. O.; Constantinides, C. P.; Anderson, H. L.; Cacialli, F.; Hayes, S. C. Resonance Raman Investigation of β-Cyclodextrin-Encapsulated π-Conjugated Polymers. J. Phys. Chem. B 2013, 117, 5737–5747. DOI: 10.1021/jp400732h.
  18. Constantinides, C. P.; Ioannou, T. A.; Koutentis, P. A. Manipulating the singlet-triplet energy gaps of arene-fused bis(1,2,3-dithiazoles): A computational study. Polyhedron 2013, 64, 172–180. DOI: 10.1016/j.poly.2013.03.054. (Invited paper for the G. Christou special issue).
  19. Constantinides, C. P.; Koutentis, P. A.; Rawson, J. M. Antiferromagnetic Interactions in 1D Heisenberg Linear Chains of 7-(4-Fluorophenyl) and 7-Phenyl-Substituted 1,3-Diphenyl-1,4-dihydro-1,2,4-benzotriazin-4-yl Radicals. Chem. Eur. J. 2012, 18, 15433–15438. DOI: 10.1002/chem.201202784.
  20. Berezin, A. A.; Constantinides, C. P.; Drouza, C.; Manoli, M.; Koutentis, P. A. From Blatter Radical to 7-Substituted 1,3-Diphenyl-1,4-dihydrothiazolo[5′,4′:4,5]benzo[1,2-e][1,2,4]triazin-4-yls: Towards Multifunctional Materials. Org. Lett. 2012, 14, 5586–5589. DOI: 10.1021/ol302714j.
  21. Constantinides, C. P.; Koutentis, P. A.; Rawson, J. M. Ferromagnetic Interactions in 1D Alternating Linear Chain of π-Stacked 1,3-Diphenyl-7-(thien-2-yl)-1,4-dihydro-1,2,4-benzotriazin-4-yl Radicals. Chem. Eur. J. 2012, 18, 7109–7116. DOI: 10.1002/chem.201200248.
  22. Constantinides, C. P.; Koutentis, P. A.; Loizou, G. Synthesis of 7-aryl/heteraryl-1,3-diphenyl-1,2,4-benzotriazinyls via palladium catalyzed Stille and Suzuki-Miyaura reactions. Org. Biomol. Chem. 2011, 9, 3122–3125. DOI: 10.1039/c1ob05167a.
  23. Constantinides, C. P.; Koutentis, P. A.; Krassos, H.; Rawson, J. M.; Tasiopoulos, A. J. Characterization and Magnetic Properties of a “Super Stable” Radical 1,3-Diphenyl-7-trifluoromethyl-1,4-dihydro-1,2,4-benzotriazin-4-yl. J. Org. Chem. 2011, 76, 2798–2806. DOI: 10.1021/jo200210s.
  24. Alberola, A.; Carter, E.; Constantinides, C. P.; Eisler, D. J.; Murphy, D. M.; Rawson, J. M. Crystal structures, EPR and magnetic properties of 2-ClC6H4CNSSN˙ and 2,5-Cl2C6H3CNNS˙. Chem. Commun. 2011, 47, 2532–2534. DOI: 10.1039/c0cc04296j.
  25. Constantinides, C. P.; Koutentis, P. A.; Schatz, J. A DFT Study of the Ground State Multiplicities of Linear vs Angular Polyheteroacenes. J. Am. Chem. Soc. 2004, 126, 16232–16241. DOI: 10.1021/ja045006t.

Book Chapters and Reviews

  1. Rawson, J. M.; Constantinides, C. P. Thiazyl Magnets. In World Scientific Reference on Spin in Organics, Vol. 4: Spin in Organics; Vardeny, Z. V.; Wohlgenannt, M., Eds.; World Scientific, 2018; pp 95–124. DOI: 10.1142/9789813230200_0002.
  2. Constantinides, C. P.; Koutentis, P. A. Stable N- and N/S-Rich Heterocyclic Radicals: Synthesis and Applications. Adv. Heterocycl. Chem. 2016, 119, 173–207. DOI: 10.1016/bs.aihch.2016.03.001. (Invited review for the “Heterocyclic Chemistry in the 21st Century – A Tribute to Alan Katritzky” volume).
  3. Koutentis, P. A.; Constantinides, C. P. 1,3,4-Thiadiazoles. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Zhdankin, V. V., Vol. Ed.; Elsevier, 2008; Vol. 5, pp 567–605. DOI: 10.1016/B978-008044992-0.00510-1.