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When Reality Defies Prediction: Polymorphism, Twinning, and Accordion Crystals.

Amy V Hall¹, Alice C Taylor¹, Natalie E Pridmore¹

¹Department of Chemistry, Durham University, Stockton Road, Durham DH1 3LE, U.K.

Journal of the American Chemical Society

|January 27, 2026

Summary

Terephthalic dihydrazide (TeDi) forms two crystal polymorphs, with Form I being experimentally stable and Form II computationally predicted as stable. A gelator template enabled preferential crystallization of Form II.

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Area of Science:

Materials Science
Crystallography
Supramolecular Chemistry

Background:

Understanding crystallization and predicting solid forms are crucial in materials science.
Terephthalic dihydrazide (TeDi) exhibits complex crystallization behavior.

Purpose of the Study:

To investigate the concomitant crystallization of terephthalic dihydrazide (TeDi) into two distinct polymorphs.
To reconcile discrepancies between experimental and computational stability predictions.
To explore methods for controlling crystallization outcomes.

Main Methods:

Solution cooling crystallization of TeDi.
Experimental characterization of polymorphs (Form I and Form II).
Computational methods including conformational analyses, lattice energy calculations, and crystal structure prediction.
Templated crystallization using a supramolecular mimetic gelator.

Main Results:

TeDi rapidly formed two concomitant polymorphs: Form I (stable, accordion-like stacks) and Form II (needle-like, transient).
Experimental data indicated Form I as the most stable polymorph.
Computational methods predicted Form II as the most stable polymorph.
A gelator template facilitated preferential crystallization of Form II.

Conclusions:

Discrepancies between experimental and computational predictions highlight the role of defects and disorder in real-world crystallization.
Remarkable crystal morphologies can arise from twinning and defects, challenging idealized models.
Supramolecular gelators can be utilized to direct and control the crystallization of specific polymorphs.