Isomorphism in a Series of Five Homologous Compounds
-diisopropylglyoxylamide derivatives (Y = H, F, Cl, Br, or I), exemplifying a rare case of isomorphism within a homologous set of achiral molecules in solution that crystallize as conglomerates by adopting a twisted chiral conformation. These enantiomorphic crystals were manually resolved using Pasteur's method, enabling direct investigation of symmetry breaking at the morphological level. Continuous chirality measures quantitatively confirm consistent chiral behavior at both the molecular and crystalline levels, while the unit cell similarity index further validates the isomorphic nature of the series. Thermal analyses reveal systematic trends in stability across the series, while crystallographic studies demonstrate the persistence of packing motifs and supramolecular chirality. Overall, this work introduces a rare class of chiral molecular materials derived from chemically distinct achiral molecules that exhibit isomorphic molecular packing. These systems are broadly relevant to fields ranging from pharmaceuticals to functional materials, where small variations in the solid-state structure can lead to substantial differences in performance.
Authors
- Lucia Maini (ORCID: https://orcid.org/0000-0002-0703-2617)
- Susobhan Das (ORCID: https://orcid.org/0000-0002-0624-6170)
- Roland C. Fischer (ORCID: https://orcid.org/0000-0001-9523-5010)
- Ferdinando Malagreca (ORCID: https://orcid.org/0000-0002-2155-1659)
- Andrew S. Dunn (ORCID: https://orcid.org/0000-0002-8417-8468)
- Priya Pandey (ORCID: https://orcid.org/0000-0002-0997-1001)
- C. Elizabeth Killalea
- Yves Henri Geerts (ORCID: https://orcid.org/0000-0002-2660-5767)
- Ryusei Oketani (ORCID: https://orcid.org/0000-0001-7860-2456)
- Roland Resel (ORCID: https://orcid.org/0000-0003-0079-3525)
- S. U. Khan (ORCID: https://orcid.org/0009-0002-1489-110X)
- Caterina Zuffa (ORCID: https://orcid.org/0000-0002-7150-3292)
- Anmol Andotra
- Jun Liu
Institutions
- Université Libre de Bruxelles (BE)
- North Carolina State University (US)
- Graz University of Technology (AT)
- Toneyama National Hospital (JP)
- Walloon Excellence in Lifesciences and Biotechnology (BE)
- International Solvay Institutes (BE)
- University of Bologna (IT)
- The University of Osaka (JP)
Publication Details
- Journal
- Crystal Growth & Design
- Published
- 2026-04-20
- DOI
- https://doi.org/10.1021/acs.cgd.6c00230
- Primary Topic
- Chemistry and Stereochemistry Studies
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Science Foundation
- Fonds De La Recherche Scientifique - FNRS
- Multidisciplinary University Research Initiative