TEACHING:
Organic Chemistry / Materials Chemistry / Dyes / Liquid Crystals / Self-Assembly
RESEARCH:
Our general area of research is best categorized as synthetic materials chemistry, which encompasses molecular design, synthesis, and materials characterization and processing. Synthesis clearly dominates our efforts that cover a wide range of synthetic methodology including modern and environmentally more benign methods, such as solvent-free and microwave assisted reactions. We are specialized in the synthesis and development of heterocyclic dyes that are mesomorphic and/or amphiphilic.
Synthesis is often preceded by the development of molecular designs that generate the desired properties. Both, molecular design and prediction of properties heavily relies on computational studies at the DFT level of theory. Synthesis is followed by the characterization of molecular and supramolecular structures and properties of the prepared compounds/materials. We are particularly well equipped for temperature dependent (polarized) spectroscopy (UV-Vis, IR, Raman, and CD) and 2D X-ray diffraction of anisotropic materials as well as their thermal analysis (DSC, TGA, and DMA). Please visit our departmental websites for more information on our shared facilities. Investigations of our compounds in devices are conducted in collaboration with other groups in North America and worldwide.
PRESENT AREAS OF INTEREST INCLUDE:
Core-only (side-chain fee) dyes, liquid crystals, and other mesophases
• Core-Only Calamitic Liquid Crystals: Molecular Design and Optoelectronic Properties. Jacob G. Rothera, Jessica Yu, Karla AlNajm, Rita Butrus, Ethan Ahangari-Bashash, Lara K. Watanabe, Jeremy M. Rawson, Anton Dmitrienko, V. Nicholas Vukotic, and S. Holger Eichhorn*, 2025, Chem. Asian. J. accepted (invited).
• Panchromatic absorption of unsymmetrical donor-acceptor dyes based on a meta-conjugated 1,3,5-heteroaryltriazine core. Jacob G. Rothera, Hi Taing, Menandro Cruz, Anton Dmitrienko, V. Nicholas Vukotic, Sean Ryno, Chad Risko,* A. Mohan Raj, William G. Skene, and S. Holger Eichhorn*, 2025, Chem. Eur. J. https://doi.org/10.1002/chem.202403860.
Mesophases as organic semiconductors and for other applications
• Core charge of imidazolium annulated triphenylene derivatives induces discotic columnar mesomorphism, Shuai Chen, Hi Taing, Mohamed Ahmida, Hong Yi He, Aiden Carr, Heidi M. Muchall* and S. Holger Eichhorn*, 2024, Soft Matter 40, 7854.
• Columnar Mesomorphism of Board-Shaped Perylene, Diketopyrrolopyrrole, Isoindigo, Indigo, and Quinoxalino-Phenanthrophenazine Dyes. S. Holger Eichhorn*, Ala’a O. El-Ballouli, Adam Cassar, and Bilal R. Kaafarani*, 2021 ChemPlusChem, 86, 319–339, doi.org/10.1002/cplu.202100024 (invited review).
• Self-Assembly of Board-Shaped Diketopyrrolopyrrole and Isoindigo Mesogens into Columnar π-π Stacks. Hi Taing, Adam Michael Cassar, Michael Udunyi Ocheje, Simon Rondeau-Gagné, Tarek H. El-Assaad, Christa A. Sharabati, Bilal R. Kaafarani*, and S. Holger Eichhorn*, 2019, ChemPlusChem (84) 103-6, doi.org/10.1002/cplu.201800524 (readers choice).
• 1,3,5-Triazine(trithiophenylcarboxylate) esters form metastable monotropic nematic discotic liquid crystal phases. Hi Taing, Jacob G. Rothera, Justin F. Binder, Charles L. B. Macdonald and S. Holger Eichhorn*, 2018, Liq. Cryst. 45 (8), 1147–1154, doi.org/10.1080/02678292.2017.1417506.
• Lateral extension induces columnar mesomorphism in crucifix shaped quinoxalinophenanthrophenazines. Ala’a O. El-Ballouli, Himadri Kayal, Chen Shuai, Tarek A. Zeidan, Farah S. Raad, Siwei Leng, Brigitte Wex, Stephen Z.D. Cheng, S. Holger Eichhorn*, and Bilal R. Kaafarani*, 2015, Tetrahedron 71, 308–14, doi.org/10.1016/j.tet.2014.11.050.
• Quasi Temperature Independent Electron Mobility in Hexagonal Columnar Mesophases of an H-Bonded Benzotristhiophene Derivative. A. Demenev, S. H. Eichhorn, T. Taerum, D. F. Perepichka, S. Patwardhan, F. C. Grozema, L. D. A. Siebbeles and R. Klenkler, Chem. Mater. 2010 (22,4) 1420-28, DOI: 10.1021/cm902453z.
Monolayers and thin films of amphiphilic organic dyes
• Amphiphilicity of Tetraazaporphyrins Containing Four TerminalCarboxylic Acid and Four Alkyl Groups Promotes Face-On Orientation in Langmuir Films, Zahra Alinia, Elmahdy Abdulhamied, Serxho Selmani, Renaud Miclette Lamarche, S. Holger Eichhorn*, Christine DeWolf*, 2024, Langmuir 2024, 40, 50, 26672–26684.
• Face- and edge-on orientations of octa-acid and -alcohol substituted tetraazaporphyrins in langmuir and Langmuir-Blodgett monolayers. M. M. Ahmida, S. Dufour, Hui–Sheng Li, H. Kayal, R. Schmidt, C. E. DeWolf and S. H. Eichhorn, Soft Matter 2013 (9,3) 811-9, DOI:10.1039/c2sm27064a.
• Cross-linking of discotic tetraazaporphyrin dyes in 2 and 3 dimensions by clickchemistry. H. Kayal, M. M. Ahmida, S. Dufour, H. Taing, S. H. Eichhorn, J. Mater. Chem. C 2013 (1,42), 7064-7072, DOI: 10.1039/C3TC31588F.
Polydiacetylene based materials
• Annealing of Acetylene Containing Cyclotriphosphazene Generates Nitrogen- and Phosphorus-Containing Led Graphitic Materialayers. M. Nazir Tahir, Audithya Nyayachavadi, Kory Schlingman, Megan Wan, S. Holger Eichhorn* and Simon Rondeau-Gagné*, 2023, New J. Chem. 47, 14002-14009.
• Amide-Assisted Polymerization of 1,3-Butadiyne Containing Thiolate Ligands on Small Gold Nanoparticles. M. Nazir Tahir, Sarah Salloum, Simon Rondeau-Gagné*, and S. Holger Eichhorn*, 2022, Langmuir, 38, 36, 10943–10952.
• Intrinsically Porous Polydiacetylene From a Functionalized Bowl-Shaped Hexaphenoxycyclotriphosphazene Derivative. M. Nazir Tahir*, Masoud Harati, Mehdi Rezapour, S. Holger Eichhorn*, Simon Rondeau-Gagné*, 2021 ACS Appl. Polym. Mater., 3 (1), 191–199, doi.org/10.1021/acsapm.0c01027.
• Topochemical Polymerization of a Nematic Tetraazaporphyrin Derivative to Generate Soluble Polydiacetylene Nanowires. M. Nazir Tahir, Elmahdy Abdulhamied, Audithya Nyayachavadi, Mariia Selivanova, S. Holger Eichhorn*, and Simon Rondeau-Gagné*, 2019, Langmuir, 35(47) 15158−15167, doi.org/10.1021/acs.langmuir.9b02187.
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