000135731 001__ 135731
000135731 005__ 20240614091947.0
000135731 0247_ $$2doi$$a10.1021/acs.chemmater.3c03241
000135731 0248_ $$2sideral$$a138774
000135731 037__ $$aART-2024-138774
000135731 041__ $$aeng
000135731 100__ $$0(orcid)0000-0003-1807-2072$$aMartínez-Bueno, Alejandro
000135731 245__ $$aEffect of Hydrogen Bonding and Chirality in Star-Shaped Molecules with Peripheral Triphenylamines: Liquid Crystal Semiconductors and Gels
000135731 260__ $$c2024
000135731 5060_ $$aAccess copy available to the general public$$fUnrestricted
000135731 5203_ $$aOrganic semiconductors with well-defined architectures pose a suitable alternative to amorphous silicon-based inorganic semiconductors. Encouraged by the development of organic semiconductors based on columnar liquid crystals, herein, we report on a family of C3-symmetric star-shaped mesogens based on triphenylamine (TPA), a functional unit with strong electron donor character. Highly stable columnar phases with high hole mobility values were obtained out of this nonplanar functional unit, and this was achieved by using flexible amide spacers to join the TPA units to a tris(triazolyl)triazine (T) star-shaped core, allowing the formation of intermolecular hydrogen bonds. The presence of hydrogen bonds results in a stabilization of the columnar architectures either in bulk or in the presence of solvents by reinforcing π-stacking and van der Waals interactions, as deduced by Fourier-transform infrared (FTIR) and X-ray diffraction (XRD) studies. Furthermore, the introduction of a stereogenic center in the flexible spacer prompts the formation of chiral aggregates in the liquid crystal state and in the organogel formed in 1-octanol, as demonstrated by circular dichroism spectroscopy.
000135731 536__ $$9info:eu-repo/grantAgreement/ES/CSIC/PIE-202260E054$$9info:eu-repo/grantAgreement/ES/DGA/E47-23R$$9info:eu-repo/grantAgreement/ES/MCIN/AEI/10.13039/501100011033$$9info:eu-repo/grantAgreement/ES/MICINN-FEDER/PID2021-122882NB-I00$$9info:eu-repo/grantAgreement/ES/MICINN/PID2021-126132NB-I00
000135731 540__ $$9info:eu-repo/semantics/openAccess$$aby$$uhttp://creativecommons.org/licenses/by/3.0/es/
000135731 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000135731 700__ $$0(orcid)0000-0001-9193-3874$$aMartín, Santiago$$uUniversidad de Zaragoza
000135731 700__ $$aOrtega, Josu
000135731 700__ $$aFolcia, César L.
000135731 700__ $$aTermine, Roberto
000135731 700__ $$aGolemme, Attilio
000135731 700__ $$0(orcid)0000-0002-7854-6316$$aGiménez, Raquel
000135731 700__ $$0(orcid)0000-0001-7091-077X$$aSierra, Teresa
000135731 7102_ $$12012$$2755$$aUniversidad de Zaragoza$$bDpto. Química Física$$cÁrea Química Física
000135731 773__ $$g36, 9 (2024), 4343-4356$$pChem. mater.$$tChemistry of materials$$x0897-4756
000135731 8564_ $$s11084687$$uhttps://zaguan.unizar.es/record/135731/files/texto_completo.pdf$$yVersión publicada
000135731 8564_ $$s3308323$$uhttps://zaguan.unizar.es/record/135731/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000135731 909CO $$ooai:zaguan.unizar.es:135731$$particulos$$pdriver
000135731 951__ $$a2024-06-14-08:58:59
000135731 980__ $$aARTICLE