Conformationally rigid molecular and polymeric naphthalene-diimides containing C6H6N2 constitutional isomers
| Autor: | Gonzalo García-Espejo, Diego Marini, Francesco Giannici, Gabriele Calabrese, Norberto Masciocchi, Candida Pipitone, Luisa Barba, Antonietta Guagliardi, Silvia Milita, Vincenzo Mirco Abbinante |
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| Přispěvatelé: | Abbinante V.M., Garcia-Espejo G., Calabrese G., Milita S., Barba L., Marini D., Pipitone C., Giannici F., Guagliardi A., Masciocchi N. |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Materials science
X ray diffraction Stacking 02 engineering and technology 010402 general chemistry 01 natural sciences NDI Ultraviolet visible spectroscopy Materials Chemistry Structural isomer Molecule Thermal stability Thin film Polymer Crystallinity Alkyl Amine Thin film solar cell chemistry.chemical_classification Organic electronics Spin coating General Chemistry 021001 nanoscience & nanotechnology 0104 chemical sciences Energy gap Isomer Nondestructive examination Crystallography chemistry 0210 nano-technology Stability Naphthalene |
| Zdroj: | Journal of materials chemistry. C 9 (2021): 10875–10888. doi:10.1039/d1tc00564b info:cnr-pdr/source/autori:Abbinante, Vincenzo Mirco; Garcia-Espejo, Gonzalo; Calabrese, Gabriele; Milita, Silvia; Barba, Luisa; Marini, Diego; Pipitone, Candida; Giannici, Francesco; Guagliardi, Antonietta; Masciocchi, Norberto/titolo:Conformationally rigid molecular and polymeric naphthalene-diimides containing C6H6N2 constitutional isomers/doi:10.1039%2Fd1tc00564b/rivista:Journal of materials chemistry. C (Print)/anno:2021/pagina_da:10875/pagina_a:10888/intervallo_pagine:10875–10888/volume:9 |
| DOI: | 10.1039/d1tc00564b |
| Popis: | Organic thin films based on naphthalenediimides (NDIs) bearing alkyl substituents have shown interesting properties for application in OLEDs, thermoelectrics, solar cells, sensors and organic electronics. However, the polymorphic versatility attributed to the flexibility of alkyl chains remains a challenging issue, with detrimental implications on the performances. Aryl analogues containing C6H6N2 constitutional isomers are herein investigated as one of the possible way-out strategies. The synthesis of molecular and polymeric species is described, starting from naphthaleneteracarboxyldianhydride with isomeric aromatic amines and hydrazine. The materials are fully characterized by spectroscopy, thermal and structural X-ray diffraction methods, both as bulk powders and thin films, revealing a rich structural landscape. Depending on the stereochemistry of the branching aryls, the compounds show a variety of parallel stacking of the NDI cores, and high structural stability upon heating, up to 560 °C in the polymeric form. Thin films prepared by spin coating from organic solvent solutions and studied by grazing-incidence X-ray diffraction exhibit a high degree of crystallinity indicating the intrinsic tendency of these molecules to self-assemble in an ordered fashion without the need for any post-processing technique. In line with other NDI-based diimides, UV-vis spectroscopy indicates the optical band gaps falling in the visible region (2.87-3.02 eV). DFT calculations reveal a significant lowering of the frontier orbital energies of the hydrazido derivative. Beyond solution processing, the high thermal stability and the absence of polymorphic forms of these materials suggest that sublimation-based routes for films and device preparation can also be followed. This journal is |
| Databáze: | OpenAIRE |
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