Photosensitive Self-Assembled Monolayers on Gold: Photochemistry of Surface-Confined Aryl Azide and Cyclopentadienylmanganese Tricarbonyl

Wollman, Eric W.; Kang, Doris; Frisbie, C. Daniel; Lorković, Ivan M.; Wrighton, Mark S.

doi:10.1021/ja00089a030

Cited by 154 publications

(131 citation statements)

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“…3) of the nitrogen 1s binding energies (BE) of diazides revealed two distinct peaks, one centered at 401 eV and another centered at 404 eV, with a 2:1 ratio of the peak areas. [27] The less intense, higher energy, 404 eV peak is unusual for covalently-bonded nitrogen, and we assign this peak to the electron-deficient nitrogen in the azide group. Reaction of the diazide with PIM-1 via the nitrene reaction led to a considerable reduction in intensity of the 404 eV peak.…”

mentioning

confidence: 84%

Azide‐based Cross‐Linking of Polymers of Intrinsic Microporosity (PIMs) for Condensable Gas Separation

Cin

Pinnau

et al. 2011

Macromol. Rapid Commun.

145

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Cross‐linked polymers of intrinsic microporosity (PIM)s for gas separation membranes, were prepared by a nitrene reaction from a representative PIM in the presence of two different diazide cross‐linkers. The reaction temperature was optimized using TGA. The homogenous membranes were cast from THF solutions of different ratios of PIM to azides. The resulting cross‐linked structures of the PIMs membranes were formed at 175 °C after 7.5 h and confirmed by TGA, XPS, FT‐IR spectroscopy and gel content analysis. These resulting cross‐linked polymeric membranes showed excellent gas separation performance and can be used for O2/N2 and CO2/N2 gas pairs, as well as for condensable gases, such as CO2/CH4, propylene/propane separation. Most importantly, and differently from typical gas separation membranes derived from glassy polymers, the crosslinked PIMs showed no obvious CO2 plasticization up to 20 atm pressure of pure CO2 and CO2/CH4 mixtures. magnified image

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mentioning

confidence: 84%

Azide‐based Cross‐Linking of Polymers of Intrinsic Microporosity (PIMs) for Condensable Gas Separation

Cin

Pinnau

et al. 2011

Macromol. Rapid Commun.

145

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“…An alternative to surface modification is seen in the SAMs of photoswitchable molecules based on cyclopentadienyl manganese tricarbonyls [HS-C 11 H 22 -CpMn(CO) 3 ] and azides employed by Wrighton and coworkers (16,17). These systems can be employed to prepare photoactive surfaces that, via photosubstitution reactions, can be used for high-resolution lateral image patterning.…”

Section: Photochemically Reactive Self-assembled Monolayers: Irreversmentioning

confidence: 99%

Light Switching of Molecules on Surfaces

Browne

Feringa

2009

Annu. Rev. Phys. Chem.

274

254

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Smart surfaces, surfaces that respond to an external stimulus in a defined manner, hold considerable potential as components in molecular-based devices, not least as discrete switching elements. Many stimuli can be used to switch surfaces between different states, including redox, light, pH, and ion triggers. The present review focuses on molecular switching through the electronic excitation of molecules on surfaces with light. In developing light-responsive surfaces, investigators face several challenges, not only in achieving high photostationary states and fully reversible switching, but also in dealing with fatigue resistance and the effect of immobilization itself on molecular properties. The immobilization of light-responsive molecules requires the design and synthesis of functional molecular components both to achieve light switching and to anchor the molecular entity onto a surface. This review discusses several demonstrative examples of photoswitchable molecular systems in which the photochemistry has been explored in the immobilized state under ambient conditions and especially on electroactive surfaces, including self-assembled monolayers, bilayers, and polymer films.

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“…The ratio of the areas of these two peaks is approximately 2:1. The peak at 402 eV corresponds to the relatively electron poor middle N atom of the azide group 32 (Please note that the peaks are shifted due to charging effects). After reaction of the pHEMA with pDVB-N 3 only one N 1s signal can be observed at 397 eV.…”

Section: Approachmentioning

confidence: 99%

Surface Modification of Poly(divinylbenzene) Microspheres via Thiol−Ene Chemistry and Alkyne−Azide Click Reactions

et al. 2009

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We report the functionalization of cross-linked poly(divinylbenzene) (pDVB) microspheres using both thiol-ene chemistry and azide-alkyne click reactions. The RAFT technique was carried out to synthesize SH-functionalized poly(N-isopropylacrylamide) (pNIPAAm) and utilized to generate pNIPAAm surface-modified microspheres via thiol-ene modification. The accessible double bonds on the surface of the microspheres allow the direct coupling with thiol-end functionalized pNIPAAm. In a second approach, pDVB microspheres were grafted with poly(2-hydroxyethyl methacrylate) (pHEMA). For this purpose, the residual double bonds on the microspheres surface were used to attach azide groups via the thiol-ene approach of 1-azido-undecane-11-thiol. In a second step, alkyne endfunctionalized pHEMA was used to graft pHEMA to the azide-modified surface via click-chemistry (Huisgen 1,3-dipolar cycloaddition). The surface-sensitive characterization methods X-ray photoelectron spectroscopy, scanning-electron microscopy and FT-IR transmission spectroscopy were employed to characterize the successful surface modification of the microspheres. In addition, fluorescence microscopy confirms the presence of grafted pHEMA chains after labeling with Rhodamine B.

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Photosensitive Self-Assembled Monolayers on Gold: Photochemistry of Surface-Confined Aryl Azide and Cyclopentadienylmanganese Tricarbonyl

Cited by 154 publications

References 0 publications

Azide‐based Cross‐Linking of Polymers of Intrinsic Microporosity (PIMs) for Condensable Gas Separation

Azide‐based Cross‐Linking of Polymers of Intrinsic Microporosity (PIMs) for Condensable Gas Separation

Light Switching of Molecules on Surfaces

Surface Modification of Poly(divinylbenzene) Microspheres via Thiol−Ene Chemistry and Alkyne−Azide Click Reactions

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