| Full text | |
| Author(s): |
de Assis, Renan Gabriel
;
de Oliveira Junior, Marcos
;
Escote, Marcia Tsuyama
;
Pinheiro, Carlos Basilio
;
Acuna, Jose Javier Saez
;
Ferreira, Fabio Furlan
;
Pedroza, Luana Sucupira
;
Brochsztain, Sergio
;
de Queiroz, Thiago Branquinho
Total Authors: 9
|
| Document type: | Journal article |
| Source: | ACS APPLIED ENGINEERING MATERIALS; v. 2, n. 7, p. 11-pg., 2024-07-08. |
| Abstract | |
Naphthalenetetracarboxylic diimides (NDIs) are efficient electron acceptors due to their high electron affinity. They are applied in heterogeneous catalysis and organic electronics. In this work, we report, for the first time, the synthesis of N,N '-bis[3-(triethoxysilyl)propyl]-1,4,5,8-naphthalenediimide (NDI-silane) as a molecular crystal obtained from recrystallization in petroleum ether. The compound is stable in air conditions and chloroform solution. Its crystal structure was determined by single-crystal X-ray diffraction. We have characterized the intermolecular dispersive interactions by density functional theory calculations, indicating that the stability of the crystal in air conditions is related to dispersive interactions. Furthermore, we characterize the optical and photoelectrical properties of thin NDI-silane films, demonstrating photoinduced conductivity over a wide range of temperatures (10-300 K). Remarkably, a venture of NDI-based organosilica can be obtained from stable NDI-silane crystals, prominent materials in organoelectronics and photocatalysis. As a proof of concept, we prepare mesoporous organosilicas with 100% NDI-silane using the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate as a templating and sol-gel catalytic agent. These materials show a well-formed organosilica network, presenting only T-3 and T-2 Si species, as probed by solid-state Si-29 NMR. As a result, the mesoporous materials are considerably more resistant to thermal degradation than the crystals, being stable up to 450 degrees C. According to N-2 adsorption isotherms and transmission electron microscopy images, they demonstrate microporous and mesoporous structures associated with narrow slitlike pores. (AU) | |
| FAPESP's process: | 23/01502-1 - Synthesis, characterization, and solubility study of new crystalline forms of antineoplastic agents |
| Grantee: | Fabio Furlan Ferreira |
| Support Opportunities: | Regular Research Grants |
| FAPESP's process: | 21/07694-4 - Investigation of naphthalenediimide and phenothiazine derivatives as photoinduced charge separation junctions |
| Grantee: | Renan Gabriel de Assis |
| Support Opportunities: | Scholarships in Brazil - Scientific Initiation |
| FAPESP's process: | 13/07793-6 - CEPIV - Center for Teaching, Research and Innovation in Glass |
| Grantee: | Edgar Dutra Zanotto |
| Support Opportunities: | Research Grants - Research, Innovation and Dissemination Centers - RIDC |
| FAPESP's process: | 17/10292-0 - Atomistic simulations of electrochemistry |
| Grantee: | Luana Sucupira Pedroza |
| Support Opportunities: | Research Grants - Young Investigators Grants |
| FAPESP's process: | 23/08771-8 - Advanced materials based on aromatic imides with applications for the energy sector |
| Grantee: | Sergio Brochsztain |
| Support Opportunities: | Regular Research Grants |
| FAPESP's process: | 22/02974-1 - Fundamental aspects of the amorphous state of metal organic compounds: a solid state magnetic resonance approach |
| Grantee: | Marcos de Oliveira Junior |
| Support Opportunities: | Research Grants - Initial Project |
| FAPESP's process: | 20/13466-1 - Design, synthesis and characterization of molecular systems for light harvesting and charge separation |
| Grantee: | Thiago Branquinho de Queiroz |
| Support Opportunities: | Research Grants - Young Investigators Grants |