Tuning the liquid crystal behavior of subphthalocyanines: effects of substitution, chirality, and hydrogen bonding

Abstract

Bowl-shaped aromatics that self-assemble into columnar liquid crystals (LCs) are key components for developing polarized semiconductors. However, progress in this field has been sluggish, as the limited set of available π-conjugated curved scaffolds has left structure–property relationships poorly understood. Herein the role that substitution pattern, substituent nature, and chirality play in the LC columnar organization of subphthalocyanines (SubPcs) is explored. Remarkably, it is revealed that enantiopure SubPcs exhibit a reduced tendency to form LC phases compared to their racemic counterparts, whereas higher substitution density increases flexibility within the columns, compromising coaxial alignment. Moreover, we find that the use of conformationally flexible, π-extended peripheral substituents enables efficient π–π stacking, and that the incorporation of hydrogen-bonding amide groups leads to highly stable mesophases with elevated melting points, although the mesophase remains at room temperature after thermal treatment. These trends are further rationalized through theoretical modeling. Overall, this work provides valuable synthetic and design guidelines for advancing bowl-shaped aromatics toward next-generation functional columnar liquid crystals.

Graphical abstract: Tuning the liquid crystal behavior of subphthalocyanines: effects of substitution, chirality, and hydrogen bonding

Supplementary files

Article information

Article type
Paper
Submitted
04 Dzi 2025
Accepted
20 Mud 2025
First published
27 Mud 2025
This article is Open Access
Creative Commons BY license

J. Mater. Chem. C, 2025, Advance Article

Tuning the liquid crystal behavior of subphthalocyanines: effects of substitution, chirality, and hydrogen bonding

J. Labella, E. López-Serrano, J. Labrador-Santiago, J. Barberá, C. L. Folcia, T. Sierra and T. Torres, J. Mater. Chem. C, 2025, Advance Article , DOI: 10.1039/D5TC01417D

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