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  1. Book ; Online: Prato Reactions of Fullerene and Metallofullerenes for the Preparation of Water-Soluble Polymers

    Aroua, Safwan

    2015  

    Abstract: Diss., Eidgenössische Technische Hochschule ETH Zürich, Nr. ... ...

    Abstract Diss., Eidgenössische Technische Hochschule ETH Zürich, Nr. 22581
    Keywords KUNSTSTOFFE (BIOMEDIZINISCHE MATERIALIEN) ; WASSERLÖSLICHE POLYMERE (CHEMIE) ; FULLERENE (MACROCYCLISCHE VERBINDUNGEN) ; METALLORGANISCHE VERBINDUNGEN ; CYCLOADDITIONEN + CYCLOREVERSIONEN + CYCLOELIMINIERUNG (CHEMISCHE REAKTIONEN) ; KOMPLEXBILDUNG (KOMPLEXCHEMIE) ; CHINOXALIN UND DERIVATE (HETEROCYCLISCHE KOHLENWASSERSTOFFE)
    Language English
    Publisher Zürich, ETH-Zürich
    Publishing country ch
    Document type Book ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  2. Thesis ; Online: Prato Reactions of Fullerene and Metallofullerenes for the Preparation of Water-Soluble Polymers

    Aroua, Safwan

    2015  

    Keywords METAL-ORGANIC COMPOUNDS ; COMPLEXATION (COMPLEX CHEMISTRY) ; PLASTICS (BIOMEDICAL MATERIALS) ; METALLORGANISCHE VERBINDUNGEN ; KOMPLEXBILDUNG (KOMPLEXCHEMIE) ; QUINOXALINE AND DERIVATIVES (HETEROCYCLIC HYDROCARBONS) ; CHINOXALIN UND DERIVATE (HETEROCYCLISCHE KOHLENWASSERSTOFFE) ; FULLERENES (MACROCYCLIC COMPOUNDS) ; FULLERENE (MACROCYCLISCHE VERBINDUNGEN) ; KUNSTSTOFFE (BIOMEDIZINISCHE MATERIALIEN) ; WATER-SOLUBLE POLYMERS (CHEMISTRY) ; WASSERLÖSLICHE POLYMERE (CHEMIE) ; CYCLOADDITIONEN + CYCLOREVERSIONEN + CYCLOELIMINIERUNG (CHEMISCHE REAKTIONEN) ; CYCLOADDITIONS + RETROCYCLOADDITIONS + CYCLOELIMINATION (CHEMICAL REACTIONS) ; info:eu-repo/classification/ddc/540 ; info:eu-repo/classification/ddc/610 ; Chemistry ; Medical sciences ; medicine
    Language English
    Publisher ETH-Zürich
    Publishing country ch
    Document type Thesis ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  3. Article: Regioselective Synthesis and Characterization of Tris- and Tetra-Prato Adducts of M₃N@C₈₀ (M = Y, Gd)

    Semivrazhskaya, Olesya / Aroua, Safwan / Yulikov, Maxim / Romero-Rivera, Adrian / Stevenson, Steven / Garcia-Borràs, Marc / Osuna, Sílvia / Yamakoshi, Yoko

    Journal of the American Chemical Society. 2020 June 26, v. 142, no. 30

    2020  

    Abstract: The tris- and tetra-adducts of M₃N@Iₕ-C₈₀ metallofullerenes were synthesized and characterized for the first time. The 1,3-dipolar cycloaddition (Prato reaction) of Y₃N@Iₕ-C₈₀ and Gd₃N@Iₕ-C₈₀ with an excess of N-ethylglycine and formaldehyde provided ... ...

    Abstract The tris- and tetra-adducts of M₃N@Iₕ-C₈₀ metallofullerenes were synthesized and characterized for the first time. The 1,3-dipolar cycloaddition (Prato reaction) of Y₃N@Iₕ-C₈₀ and Gd₃N@Iₕ-C₈₀ with an excess of N-ethylglycine and formaldehyde provided tris- and tetra-fulleropyrrolidine adducts in a regioselective manner. Purification by HPLC and analyses of the isolated peaks by NMR, MS, and vis-NIR spectra revealed that the major products were four tris- and one tetra-isomers for both Y₃N@Iₕ-C₈₀ and Gd₃N@Iₕ-C₈₀. Considering the large number of possible isomers (e.g., at least 1140 isomers for the tris-adduct), the limited number of isomers obtained indicated that the reactions proceeded with high regioselectivity. NMR analyses of the Y₃N@Iₕ-C₈₀ adducts found that the tris-adducts were all-[6,6]- or [6,6][6,6][5,6]-isomers and that some showed mutual isomerization or remained intact at room temperature. The tetra-adduct obtained as a major product was all-[6,6] and stable. For the structural elucidation of Gd₃N@Iₕ-C₈₀ tris- and tetra-adducts, density functional theory (DFT) calculations were performed to estimate the relative stabilities of tris- and tetra-adducts formed upon Prato functionalization of the most pyramidalized regions of the fullerene structure. The most stable structures corresponded to additions on the most pyramidalized (i.e., strained) bonds. Taking together the experimental vis-NIR spectra, NMR assignments, and the computed relative DFT stabilities of the potential tris- and tetra-adducts, the structures of the isolated adducts were elucidated. Electron resonance (ESR) measurements measurements of pristine, bis-, and tris-adducts of Gd₃N@C₈₀ suggested that the rotation of the endohedral metal cluster slowed upon increase of the addition numbers to C₈₀ cage, which is favored for accommodating the Gd atoms of the relatively large Gd₃N cluster inner space at the sp³ addition sites. This is presumably related to the high regioselectivity in the Prato addition reaction driven by the strain release of the Gd₃N@C₈₀ fullerene structure.
    Keywords ambient temperature ; cycloaddition reactions ; density functional theory ; formaldehyde ; fullerene ; isomerization ; regioselectivity
    Language English
    Dates of publication 2020-0626
    Size p. 12954-12965.
    Publishing place American Chemical Society
    Document type Article
    Note NAL-AP-2-clean
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.9b13768
    Database NAL-Catalogue (AGRICOLA)

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  4. Article ; Online: Prato reaction of M3N@I(h)-C80 (M = Sc, Lu, Y, Gd) with reversible isomerization.

    Aroua, Safwan / Yamakoshi, Yoko

    Journal of the American Chemical Society

    2012  Volume 134, Issue 50, Page(s) 20242–20245

    Abstract: The 1,3-dipolar cycloaddition of an azomethine ylide (Prato reaction) with M(3)N@I(h)-C(80) (denoted as M(3)N@C(80); M = Sc, Lu, Y, Gd) was carried out to obtain fulleropyrrolidinebis(carboxylic acid) derivatives as scaffolds for the preparation of ... ...

    Abstract The 1,3-dipolar cycloaddition of an azomethine ylide (Prato reaction) with M(3)N@I(h)-C(80) (denoted as M(3)N@C(80); M = Sc, Lu, Y, Gd) was carried out to obtain fulleropyrrolidinebis(carboxylic acid) derivatives as scaffolds for the preparation of various functionalized M(3)N@C(80) materials. The formation of two monoadduct isomers (the [6,6]- and [5,6]-adducts) were detected by HPLC and identified by NMR and vis/NIR spectroscopies. In each Prato reaction with M(3)N@C(80), the initial addition gave a [6,6]-adduct of the I(h)-C(80) cage, and subsequently, a [5,6]-adduct was obtained by complete or partial thermal isomerization via a rearrangement reaction. The reaction rate of the latter thermal conversion of the adducts was dependent on the size of the metal cluster inside C(80), and interestingly, in the reactions of Y(3)N@C(80) and Gd(3)N@C(80), this conversion was found to be reversible for the first time. Detailed kinetic studies provided the enthalpy and entropy barriers for the reactions of the adducts of Lu(3)N@C(80), Y(3)N@C(80), and Gd(3)N@C(80). The utility of the obtained Prato adducts was confirmed by preparation of a highly water-soluble Gd(3)N@C(80) derivative.
    Language English
    Publishing date 2012-12-19
    Publishing country United States
    Document type Journal Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/ja309550z
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Micelle vs. vesicle formation controlled by distal functionalization of C

    Tiu, Elisha G V / Liosi, Korinne / Aroua, Safwan / Yamakoshi, Yoko

    Journal of materials chemistry. B

    2017  Volume 5, Issue 32, Page(s) 6676–6680

    Abstract: An amphiphilic ... ...

    Abstract An amphiphilic C
    Language English
    Publishing date 2017-08-03
    Publishing country England
    Document type Journal Article
    ZDB-ID 2702241-9
    ISSN 2050-7518 ; 2050-750X
    ISSN (online) 2050-7518
    ISSN 2050-750X
    DOI 10.1039/c7tb00829e
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article: Prato Reaction of M3N@Ih-C80 (M = Sc, Lu, Y, Gd) with Reversible Isomerization

    Aroua, Safwan / Yamakoshi Yoko

    Journal of the American Chemical Society. 2012 Dec. 19, v. 134, no. 50

    2012  

    Abstract: The 1,3-dipolar cycloaddition of an azomethine ylide (Prato reaction) with M₃N@Iₕ-C₈₀ (denoted as M₃N@C₈₀; M = Sc, Lu, Y, Gd) was carried out to obtain fulleropyrrolidinebis(carboxylic acid) derivatives as scaffolds for the preparation of ... ...

    Abstract The 1,3-dipolar cycloaddition of an azomethine ylide (Prato reaction) with M₃N@Iₕ-C₈₀ (denoted as M₃N@C₈₀; M = Sc, Lu, Y, Gd) was carried out to obtain fulleropyrrolidinebis(carboxylic acid) derivatives as scaffolds for the preparation of various functionalized M₃N@C₈₀ materials. The formation of two monoadduct isomers (the [6,6]- and [5,6]-adducts) were detected by HPLC and identified by NMR and vis/NIR spectroscopies. In each Prato reaction with M₃N@C₈₀, the initial addition gave a [6,6]-adduct of the Iₕ-C₈₀ cage, and subsequently, a [5,6]-adduct was obtained by complete or partial thermal isomerization via a rearrangement reaction. The reaction rate of the latter thermal conversion of the adducts was dependent on the size of the metal cluster inside C₈₀, and interestingly, in the reactions of Y₃N@C₈₀ and Gd₃N@C₈₀, this conversion was found to be reversible for the first time. Detailed kinetic studies provided the enthalpy and entropy barriers for the reactions of the adducts of Lu₃N@C₈₀, Y₃N@C₈₀, and Gd₃N@C₈₀. The utility of the obtained Prato adducts was confirmed by preparation of a highly water-soluble Gd₃N@C₈₀ derivative.
    Keywords enthalpy ; entropy ; high performance liquid chromatography ; isomerization ; isomers ; nuclear magnetic resonance spectroscopy ; organic compounds
    Language English
    Dates of publication 2012-1219
    Size p. 20242-20245.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021%2Fja309550z
    Database NAL-Catalogue (AGRICOLA)

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  7. Article ; Online: Regioselective Synthesis and Characterization of Tris- and Tetra-Prato Adducts of M

    Semivrazhskaya, Olesya / Aroua, Safwan / Yulikov, Maxim / Romero-Rivera, Adrian / Stevenson, Steven / Garcia-Borràs, Marc / Osuna, Sílvia / Yamakoshi, Yoko

    Journal of the American Chemical Society

    2020  Volume 142, Issue 30, Page(s) 12954–12965

    Abstract: The tris- and tetra-adducts of ... ...

    Abstract The tris- and tetra-adducts of M
    Language English
    Publishing date 2020-07-17
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.9b13768
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Bonn / Germany

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  8. Article: C60 Pyrrolidine Bis-carboxylic Acid Derivative as a Versatile Precursor for Biocompatible Fullerenes

    Aroua, Safwan / Schweizer W. Bernd / Yamakoshi Yoko

    Organic letters. 2014 Mar. 21, v. 16, no. 6

    2014  

    Abstract: A C₆₀ Prato derivative with bis-ᵗBu ester was prepared as a stable and convenient scaffold for the development of fullerene derivatives such as water-soluble C₆₀–PEG conjugates, fulleropeptides via solid phase synthesis, and bis- ... ...

    Abstract A C₆₀ Prato derivative with bis-ᵗBu ester was prepared as a stable and convenient scaffold for the development of fullerene derivatives such as water-soluble C₆₀–PEG conjugates, fulleropeptides via solid phase synthesis, and bis-functionalized C₆₀.
    Keywords chemical reactions ; chemical structure ; fullerene ; organic compounds
    Language English
    Dates of publication 2014-0321
    Size p. 1688-1691.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1523-7052
    DOI 10.1021%2Fol500363r
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  9. Article: Micelle vs. vesicle formation controlled by distal functionalization of C60–PEG conjugates

    Tiu, Elisha G. V / Liosi, Korinne / Aroua, Safwan / Yamakoshi, Yoko

    Journal of materials chemistry B. 2017 Aug. 16, v. 5, no. 32

    2017  

    Abstract: An amphiphilic C60–PEG conjugate was modified by the addition of cationic moieties in the hydrophobic C60 part to provide the related bis- and tris-adducts and their self-assembling structures were compared. All of these materials were water-soluble and ... ...

    Abstract An amphiphilic C60–PEG conjugate was modified by the addition of cationic moieties in the hydrophobic C60 part to provide the related bis- and tris-adducts and their self-assembling structures were compared. All of these materials were water-soluble and their supramolecular structures were investigated in the aqueous phase using tensiometry, DLS, and STEM techniques. While mono- and bis-adducts formed micelle-type supramolecular structures, the tris-one with two additional cationic pyrrolidine groups showed the formation of larger particles as indicated by DLS data. Further, the STEM image of the tris-adduct showed a vesicle-type supramolecular structure with, presumably, an internal water-phase inside.
    Keywords hydrophobicity ; micelles ; moieties ; water solubility
    Language English
    Dates of publication 2017-0816
    Size p. 6676-6680.
    Publishing place The Royal Society of Chemistry
    Document type Article
    ZDB-ID 2702241-9
    ISSN 2050-7518 ; 2050-750X
    ISSN (online) 2050-7518
    ISSN 2050-750X
    DOI 10.1039/c7tb00829e
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  10. Article ; Online: C60 pyrrolidine bis-carboxylic acid derivative as a versatile precursor for biocompatible fullerenes.

    Aroua, Safwan / Schweizer, W Bernd / Yamakoshi, Yoko

    Organic letters

    2014  Volume 16, Issue 6, Page(s) 1688–1691

    Abstract: A C60 Prato derivative with bis-(t)Bu ester was prepared as a stable and convenient scaffold for the development of fullerene derivatives such as water-soluble C60-PEG conjugates, fulleropeptides via solid phase synthesis, and bis-functionalized C60. ...

    Abstract A C60 Prato derivative with bis-(t)Bu ester was prepared as a stable and convenient scaffold for the development of fullerene derivatives such as water-soluble C60-PEG conjugates, fulleropeptides via solid phase synthesis, and bis-functionalized C60.
    MeSH term(s) Carboxylic Acids/chemistry ; Fullerenes/chemistry ; Molecular Structure ; Pyrrolidines/chemistry ; Water/chemistry
    Chemical Substances Carboxylic Acids ; Fullerenes ; Pyrrolidines ; Water (059QF0KO0R) ; pyrrolidine (LJU5627FYV)
    Language English
    Publishing date 2014-03-21
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/ol500363r
    Database MEDical Literature Analysis and Retrieval System OnLINE

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