000161052 001__ 161052
000161052 005__ 20251017144601.0
000161052 0247_ $$2doi$$a10.1039/d5tc01417d
000161052 0248_ $$2sideral$$a144290
000161052 037__ $$aART-2025-144290
000161052 041__ $$aeng
000161052 100__ $$aLabella, Jorge
000161052 245__ $$aTuning the liquid crystal behavior of subphthalocyanines: effects of substitution, chirality, and hydrogen bonding
000161052 260__ $$c2025
000161052 5060_ $$aAccess copy available to the general public$$fUnrestricted
000161052 5203_ $$aBowl-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.
000161052 536__ $$9info:eu-repo/grantAgreement/ES/DGA/E47-23R$$9info:eu-repo/grantAgreement/ES/MCIU/PID2021-122882NB-I00$$9info:eu-repo/grantAgreement/ES/MCIU/PID2021-126132NB-I00$$9info:eu-repo/grantAgreement/ES/MCIU/PID2023-150255NB-I00$$9info:eu-repo/grantAgreement/ES/MCIU/PID2023-151167NB-I00$$9info:eu-repo/grantAgreement/ES/MICINN/CEX2020-001039-S$$9info:eu-repo/grantAgreement/ES/MICINN/CEX2023-001286-S$$9info:eu-repo/grantAgreement/EUR/MICINN/TED2021-131255B-C43
000161052 540__ $$9info:eu-repo/semantics/openAccess$$aby$$uhttps://creativecommons.org/licenses/by/4.0/deed.es
000161052 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000161052 700__ $$aLópez-Serrano, Elisa
000161052 700__ $$aLabrador-Santiago, Jorge
000161052 700__ $$0(orcid)0000-0001-5816-7960$$aBarberá, Joaquín$$uUniversidad de Zaragoza
000161052 700__ $$aFolcia, César L.
000161052 700__ $$0(orcid)0000-0001-7091-077X$$aSierra, Teresa
000161052 700__ $$aTorres, Tomás
000161052 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000161052 773__ $$g(2025), [6 pp.]$$pJ. mater. chem. C$$tJOURNAL OF MATERIALS CHEMISTRY C$$x2050-7526
000161052 8564_ $$s1475023$$uhttps://zaguan.unizar.es/record/161052/files/texto_completo.pdf$$yVersión publicada
000161052 8564_ $$s2368642$$uhttps://zaguan.unizar.es/record/161052/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000161052 909CO $$ooai:zaguan.unizar.es:161052$$particulos$$pdriver
000161052 951__ $$a2025-10-17-14:14:09
000161052 980__ $$aARTICLE