ChemInform Abstract: Chemistry and Kinetics of Singlet (Pentafluorophenyl)nitrene.

Poe, R.; Schnapp, K. A.; Young, Matthew; Grayzar, Jennifer; Platz, Matthew S.

doi:10.1002/chin.199240102

Cited by 3 publications

(4 citation statements)

References 1 publication

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“…After LbL deposition, the multilayer films were cross-linked by UV irradiation. As shown in Figure S2, a decrease in the absorbance at 270 nm is observed with UV irradiation, indicating that the azido groups are decomposed. ,,− The FT-IR absorbance of azido groups also decreases with UV irradiation (Figure d). Both the UV–vis and FT-IR results indicate that photoreaction occurs between the azido groups and the adjacent C–H bonds.…”

Section: Resultsmentioning

confidence: 93%

Layer-by-Layer Assembly of Azulene-Based Supra-Amphiphiles: Reversible Encapsulation of Organic Molecules in Water by Charge-Transfer Interaction

Zhang

Song

et al. 2013

Langmuir

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Stable multilayer films have been fabricated on the basis of alternating layer-by-layer assembly of an azulene-based supra-amphiphile and a photoreactive polyanion. Moreover, one component of the supra-amphiphile, pyrene, can be removed from the multilayer films, generating functional surface-imprinted multilayer films. Uptake experiments show that the surface-imprinted films are capable of recognizing the hydrophobic template molecule in water. The reloading process increases with increasing of temperature. The loading capacity can be regulated by change of the layer pairs. In addition, the as-prepared multilayers are promising in purification of pyrene-polluted water.

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Section: Resultsmentioning

confidence: 93%

Layer-by-Layer Assembly of Azulene-Based Supra-Amphiphiles: Reversible Encapsulation of Organic Molecules in Water by Charge-Transfer Interaction

Zhang

Song

et al. 2013

Langmuir

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“…The created covalent bonding between BA and PSC is necessary for solvent resistance and photo-patternability. (iv) A much higher proportion of BA underwent selfcrosslinking described in (ii) rather than crosslinking with PSC in (iii), since the reactivity of cyclization is seven times faster than that of azide/C-H insertion 29,30 . Therefore, the PSC aggregation was hardly disrupted, resulting in maintained charge transport pathways.…”

Section: Resultsmentioning

confidence: 98%

“…Based on the above observations, we hypothesize that the difference in reactivity may be contributing. BA may mostly have reacted with its double bonds to create a rubber matrix 29,30 , instead of reacting with the side chains of semiconductor that will disrupt chain packing and aggregation, thus able to maintain its charge transport pathway. The higher reactivity of azide/C=C cycloaddition than that of azide/C-H insertion is supported by thermogravimetric analysis (TGA) and attenuated totalreflectance Fourier transformation infrared spectroscopy (ATR-FTIR) (Supplementary Figs.…”

Section: Resultsmentioning

confidence: 99%

A molecular design approach towards elastic and multifunctional polymer electronics

Zheng

Zhang

et al. 2021

Nat Commun

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Next-generation wearable electronics require enhanced mechanical robustness and device complexity. Besides previously reported softness and stretchability, desired merits for practical use include elasticity, solvent resistance, facile patternability and high charge carrier mobility. Here, we show a molecular design concept that simultaneously achieves all these targeted properties in both polymeric semiconductors and dielectrics, without compromising electrical performance. This is enabled by covalently-embedded in-situ rubber matrix (iRUM) formation through good mixing of iRUM precursors with polymer electronic materials, and finely-controlled composite film morphology built on azide crosslinking chemistry which leverages different reactivities with C–H and C=C bonds. The high covalent crosslinking density results in both superior elasticity and solvent resistance. When applied in stretchable transistors, the iRUM-semiconductor film retained its mobility after stretching to 100% strain, and exhibited record-high mobility retention of 1 cm2 V−1 s−1 after 1000 stretching-releasing cycles at 50% strain. The cycling life was stably extended to 5000 cycles, five times longer than all reported semiconductors. Furthermore, we fabricated elastic transistors via consecutively photo-patterning of the dielectric and semiconducting layers, demonstrating the potential of solution-processed multilayer device manufacturing. The iRUM represents a molecule-level design approach towards robust skin-inspired electronics.

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“…This is justified since phenyl azide releases N 2 upon thermal activation to form the highly reactive singlet phenyl nitrene. 19 Figure 3f,g shows the energetically optimized structure for the simulated 1 × 1-PFPN/GaP(110) surface. This compact PFPN stacking is stable with the phenyl rings vertically oriented and bonded to the surface through the remaining N atom.…”

mentioning

confidence: 99%

Covalent Functionalization of GaP(110) Surfaces via a Staudinger-Type Reaction with Perfluorophenyl Azide

Ugeda

Bradley²,

Rodrigo³

et al. 2016

J. Phys. Chem. C

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Despite the markedly low chemical reactivity of the nonpolar (110) surfaces of III−V semiconductors, the covalent functionalization of GaP(110) surfaces with perfluorophenyl azide (PFPA) molecules by a Staudinger-type reaction occurs only slightly above room temperature (325 K). Scanning tunneling microscopy observations, combined with density functional theory calculations, support the formation of stable, covalent perfluorophenyl nitride (PFPN) molecule−surface bonds, which can be described as Lewis acidic Ga-stabilized phosphine imides. π−π stacking between aromatic, electron-deficient PFPN units results in compact, commensurate 2D molecular assembly at the surface. PFPA deposition on GaP(110) at room temperature with no additional annealing leads to an intermediate phase consistent with an alternating 1D array of physisorbed and chemisorbed molecular units. This work provides a new route for covalently bonding molecular linkages to the (110) surfaces of III−V semiconductors.

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ChemInform Abstract: Chemistry and Kinetics of Singlet (Pentafluorophenyl)nitrene.

Cited by 3 publications

References 1 publication

Layer-by-Layer Assembly of Azulene-Based Supra-Amphiphiles: Reversible Encapsulation of Organic Molecules in Water by Charge-Transfer Interaction

Layer-by-Layer Assembly of Azulene-Based Supra-Amphiphiles: Reversible Encapsulation of Organic Molecules in Water by Charge-Transfer Interaction

A molecular design approach towards elastic and multifunctional polymer electronics

Covalent Functionalization of GaP(110) Surfaces via a Staudinger-Type Reaction with Perfluorophenyl Azide

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