Competing Pathways in <i>N</i>-Allylurea Adsorption on Si(111)-(7 × 7)

Renzi, Valentina De; Arnaud, Gaëlle F.; Pennino, U. del

doi:10.1021/jp2103726

Cited by 4 publications

(4 citation statements)

References 40 publications

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“…The ZnO (101̅ 0) crystal was cleaned by Ar + sputtering (1 keV, 10 μA) and annealing (800 °C) cycles. The deposition of nitrocatechol on the clean ZnO surface was performed in UHV through a molecular beam evaporator 41 and investigated by means of XPS and UPS as a function of coverage. The electronic properties of the system were studied by means of XPS, UPS and HREELS.…”

Section: ■ Methodsmentioning

confidence: 99%

Nitrocatechol/ZnO Interface: The Role of Dipole in a Dye/Metal-Oxide Model System

et al. 2014

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The electronic properties of a prototype system suitable for dye-sensitized solar cell applications are investigated both experimentally and theoretically by means of electron spectroscopies (high-resolution electron energy loss spectroscopy, HREELS, and ultraviolet and X-ray photoemission spectroscopies, UPS and XPS) and first-principles density functional theory (DFT)-based calculations. The comparison of HREELS and UPS data with the DFT results allows the microscopic description of electronic structure modifications upon interface formation, and provides a quantitative evaluation of the ionization energy and electron affinity changes induced by functionalization: these variations can be associated to the electric dipole of the functional species and, thus, to the formation of an interface dipole layer

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Section: ■ Methodsmentioning

confidence: 99%

Nitrocatechol/ZnO Interface: The Role of Dipole in a Dye/Metal-Oxide Model System

et al. 2014

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“…In the O1s spectrum, BEs at 531.1, 532.3, and 533.4 eV supported the coexistence of C– O of −CO O H and −CH 2 O H, C O , and −CN( O H), respectively (Figure S4c and Table S9). , …”

Section: Resultsmentioning

confidence: 99%

“…S9). 44,45 In FCPs, the optimum population of −CONH, −CON, and −COOH should form a stable supramolecular architecture through electrostatic and hydrogen-bonding interactions, encouraging aggregation-induced n−π* and π−π* transitions and increasing I/I 0 (Figure 2). Thus, to optimize FCPs, I/I 0 values were measured after adding 35% water to the FCP4/ dimethyl sulfoxide (DMSO) solution.…”

Section: Computational Studies For Determining Heteroatomic Ntls In Fcpsmentioning

confidence: 99%

Synthesis of Intrinsically Dual-Emissive Aliphatic Conducting Polymer and ESIPT-Associated Switching of Amide-Aggregate to Imidol-Aggregate for Sensing of Cr(III) and Fe(III)

Mitra,

Sanfui,

Roy

et al. 2023

Macromolecules

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The design, synthesis, and optimization of excited-state intramolecular proton transfer (ESIPT)-associated dual-emissive aliphatic conductive polymer is one of the very challenging tasks, and has not been reported to date. Herein, aliphatic fluorescent conducting polymers (FCPs) are synthesized by polymerizing N-(monomethylol)acrylamide (MMA), acrylic acid (AA), and in situ-generated 3-N-(monomethylolacrylamido)propanoic acid (NMMAPA). Of different FCPs, the maximum population of heteroatomic nontraditional luminophores, i.e., secondary amide (−CONH), imidol (−CN(OH)), tertiary amide (−CON), and carboxylic acid (−COOH), in FCP4 is supported by the spectroscopic analyses, thermal profiles, fluorescence enhancements, and computational calculations. Thus, further investigations are made on FCP4 to explore the photophysical properties, check the suitability in dual metal ion sensing, and study the proton conductivity. The ESIPT-associated dual light emissions at 436 nm (λem1) and 573/617 nm (λem2) originate from FCP4 (amide)/FCP4 (amide)-aggregate and FCP4 (imidol)/FCP4 (imidol)-aggregate, respectively, and are supported by concentration-dependent emissions, time-correlated single photon counting studies, solvent polarity effects, and computational measurements. Regarding this, the high fluorescence quantum yields of 0.68 and 0.18 at λem1 and λem2, respectively, confirmed the ESIPT-associated strong dual emissions of FCP4. The UV spectrum within 264–300 nm, FTIR peak at 2165 cm–1, binding energies of −CN(OH)/–CN(OH) at 399.0/533.4 eV, and computational studies indicate the coexistence of FCP4 (amide)/FCP4 (amide)-aggregate and FCP4 (imidol)/FCP4 (imidol)-aggregate forms of FCP4. In FCP4, −CONH/–CN(OH)/–CON/–COOH/–CH2OH-associated dipolar and hydrogen-bonding interactions, n−π* transitions, and N-branching-associated rigidity contribute to ESIPT-associated amide–imidol phototautomerism, aggregation-enhanced emissions, dual light emissions, metal ion sensing, and conductivity. The strong coordinations of Fe(III) and Cr(III) with FCP4 (amide) and FCP4 (imidol), respectively, are supported by spectroscopic, thermal, and computational studies. The strong quenching efficiencies of Fe(III) and Cr(III) are indicated by the very low limits of detection of 0.1142 and 0.0534 ppb, respectively. The I–V and ac impedance spectroscopy data of FCP4 having 0.28 cm thickness and 1.72 cm2 area indicate high proton conductivities of 3.53 × 10–5 and 3.22 × 10–5 S cm–1 at pH = 7.0 and 8.0, respectively.

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“…This surface provides a number of chemically, spatially, and electronically inequivalent reactive sites, including the adatoms and rest atoms in both the faulted and unfaulted halves, and the corner holes. The adjacent adatom–rest atom pair on the Si(111)-(7 × 7) surface can serve as a reactive functional group to readily react with unsaturated organic functionalities, leading to di-σ binding mode through the cycloaddition-like strategy. − …”

Section: Introductionmentioning

confidence: 99%

Dissociative Adsorption of 3-Chloropropyne on Si(111)-(7 × 7): Binding and Structure

et al. 2013

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To achieve silicon functionalization for the development of hybrid devices, multifunctional molecules may be employed to attach to the silicon surfaces. It is important to get a fundamental understanding about the molecule/silicon interface chemistry and the binding configuration. The surface chemistry of 3-chloropropyne (HC≡C-CH(2)Cl) on the Si(111)-(7 × 7) surface, as a model system for understanding the interaction of the multifunctional molecules with a silicon surface, was studied by X-ray photoelectron spectroscopy (XPS), high-resolution electron energy loss spectroscopy (HREELS), and density functional theory (DFT). The 3-chloropropyne adsorbs molecularly on the silicon surface at 110 K. A chemical reaction clearly occurs such that 3-choloropropyne bonds onto the Si(111)-(7 × 7) surface at room temperature by forming C-Si linkage through the cleavage of C-Cl bond, and preserving the ethyne C≡C triple bond. This functionalized silicon surface may act as an intermediate for the growth of multiple organic layers by further attaching other functional molecules.

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Competing Pathways in N-Allylurea Adsorption on Si(111)-(7 × 7)

Cited by 4 publications

References 40 publications

Nitrocatechol/ZnO Interface: The Role of Dipole in a Dye/Metal-Oxide Model System

Nitrocatechol/ZnO Interface: The Role of Dipole in a Dye/Metal-Oxide Model System

Synthesis of Intrinsically Dual-Emissive Aliphatic Conducting Polymer and ESIPT-Associated Switching of Amide-Aggregate to Imidol-Aggregate for Sensing of Cr(III) and Fe(III)

Dissociative Adsorption of 3-Chloropropyne on Si(111)-(7 × 7): Binding and Structure

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