Synthesis and characterization of polyhedral oligomeric azido‐octaphenylsilsesquioxane

Abstract

Polyhedral oligomeric azido-octaphenylsilsesquioxane (N 3 -OPS) was synthesized from octaaminophenylsilsesquioxane (OAPS) via its diazonium salt. The synthesis included nitration of octaphenylsilsesquioxane (OPS) to octanitrophenylsilsesquioxane (ONPS), conversion of ONPS into octaaminophenylsilsesquioxane (OAPS), and conversion of OAPS into N 3 -OPS. The kinetics of the conversion of OAPS into N 3 -OPS were studied by recording the volume of N 2 gas released with the reaction time, which revealed it to be a 1st order reaction. proposed that the diazonium salt of OAPS was substituted by the main AN 3 group and a few of the AOH groups. The ratio of AN 3 :AOH was calculated to be approximately 68:32 in N 3 -OPS on the basis of the elemental analysis and 1 H-NMR. XRD suggested that N 3 -OPS was a kind of amorphous compound. The two-step conversion mechanism of OAPS to N 3 -OPS was briefly discussed. TGA results showed that N 3 -OPS was stable at ambient temperature.

Flame-Retardant Polyimide Cross-Linked with Polyhedral Oligomeric Octa(aminophenyl)silsesquioxane

“…Octa­(aminophenyl)­silsesquioxane (OAPS) was synthesized from OPS by methods detailed in the literature. , OAPS, 1 H nuclear magnetic resonance (NMR) spectroscopy (500 MHz, DMSO- d 6 , δ): 7.4–6.2 (2.0H, Ar H), 5.4–4.5 (1.0H, −NH 2 ). 29 Si solid NMR (400 MHz, δ): −68.3, −77.5.…”

“…In our previous studies, , OAPS was prepared in tetrahydrofuran using hydrazine hydrate as reductant from octa­(nitrophenyl)­silsesquioxane (ONPS) in 1 h on the 5% Pd/C-FeCl 3 catalyst (Scheme ). In the present work, PI composites cross-linked through OAPS were prepared.…”

“…literature 29,30. OAPS,1 H nuclear magnetic resonance (NMR) spectroscopy (500 MHz, DMSO-d 6 , δ): 7.4−6.2 (2.0H, Ar H), 5.4−4.5 (1.0H, −NH 2 ).…”

Curing and thermal behaviors of inorganic–organic hybrid polyarylacetylene resins with polyhedral oligomeric octa(propargylaminophenyl)silsesquioxane

“…Octa(aminophenyl)silsesquioxane (OAPS) was synthesized from OPS by the method described in the literature 27–29. OAPS: 1 H‐nuclear magnetic resonance (NMR) spectroscopy (500 MHz, DMSO‐d 6 , δ): 7.4–6.2 (2.0H, Ar H), 5.4–4.5 (1.0H, –NH 2 ); 29 Si solid NMR (400 MHz, δ): −68.3, −77.5; 13 C‐NMR (500 MHz, DMSO‐d 6 , δ): 153.2, 147.9, 135.1, 131.4, 128.6, 121.2, 119.3, 116.4, 114.6, 113.3; Fourier transform‐infrared (FTIR) spectroscopy (KBr): ν = 3456 and 3358 (‐NH 2 ), 1115 (SiO) cm −1 ; Analysis calculated for OAPS: C 50.…”

“…In our previous work, 26 a novel polyhedral oligomeric octa(propargylaminophenyl)silsesquioxane (OPAPS, (SiO 1.5 C 6 H 4 NHCH 2 CBCH) 8 ) was prepared from octaphenylsilsesquioxane (OPS) via octa(aminophenyl)silsesquioxane (OAPS) by following the literature methods (Scheme 2). [27][28][29] The terminal alkynyl groups in OPAPS could participate in the thermal curing process of prePAA. In this study, we investigated the thermal curing reactions of prePAA composites based on OPAPS, and the thermal behaviors of the curing products have been analyzed.…”