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Financial support from the Spanish MCIN/AEI/10.13039/501100011033 and European Union NextGenerationEU/PRTR (TED2021-131255B-C43), MCIU/AEI/10.13039/501100011033/FEDER, UE (PID) (PID2023-151167NB-I00, PID2021-122882NB-I00, PID2021-126132NB-I00 and PID2023-150255NB-I00), the Comunidad de Madrid and the Spanish State through the Recovery, Transformation and Resilience Plan ["Materiales Disruptivos Bidimensionales (2D)" (MAD2D-CM) (UAM1)-MRR Materiales Avanzados], the Gobierno de Aragon- FSE (E47_23R-research group), the Basque Government project IT1458-22, and the European Union through the Next Generation EU funds is fully acknowledged. IMDEA Nanociencia acknowledges support from the "Severo Ochoa" Programme for Centres of Excellence in R&D (MINECO, CEX2020-001039-S). INMA acknowledges support from the "Severo Ochoa" Programme for Centres of Excellence in R&D (MCIN, CEX2023-001286-S). E. L. S. acknowledges MECD, Spain, for a F. P. U. Fellowship.

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

Publicated to:JOURNAL OF MATERIALS CHEMISTRY C (): - - 2025-05-27 (), DOI: 10.1039/d5tc01417d

Authors: Labella J; López-Serrano E; Labrador-Santiago J; Barberá J; Folcia CL; Sierra T; Torres T

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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 pi-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, pi-extended peripheral substituents enables efficient pi-pi 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.

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