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  • 1.
    Blom, Magnus
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Olsson, Sandra
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Norrehed, Sara
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Andersson, Claes-Henrik
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Grennberg, Helena
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Photomodulable bis-porphyrin molecular tweezers as dynamic host systems for diamine guestsManuscript (preprint) (Other academic)
    Abstract [en]

    Bisporphyrin molecular tweezers with an enediyne (1) or a stiff stilbene (2) photoswitchable spacer are proposed as systems for modulation of bitopic binding to diamine guests via E/Z photoisomerization. The photoisomerization has been monitored by UV-Vis and 1H NMR spectroscopy and occurs without side reactions such as Bergman cyclization. Possible applications are rationalized in terms of competitive binding involving monoamine/diamine mixtures, and are supported by conformational analysis of the envisioned host-guest complexes. Binding dynamics for conformationally flexible guests show significantly different performance of aliphatic 1,w-diamine guests with varying N-N distance.

  • 2.
    Bunrit, Anon
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Dahlstrand, Christian
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Olsson, Sandra K.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Srifa, Pemikar
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Huang, Genping
    Orthaber, Andreas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Sjöberg, Per J. R.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Analytical Chemistry.
    Biswas, Srijit
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Himo, Fahmi
    Samec, Joseph S. M.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Bronsted Acid-Catalyzed Intramolecular Nucleophilic Substitution of the Hydroxyl Group in Stereogenic Alcohols with Chirality Transfer2015In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 137, no 14, p. 4646-4649Article in journal (Refereed)
    Abstract [en]

    The hydroxyl group of enantioenriched benzyl, propargyl, allyl, and alkyl alcohols has been intramolecularly displaced by uncharged O-, N-, and S-centered nucleophiles to yield enantioenriched tetrahydrofuran, pyrrolidine, and tetrahydrothiophene derivatives with phosphinic acid catalysis. The five-membered heterocyclic products are generated in good to excellent yields, with high degree of chirality transfer, and water as the only side-product. Racemization experiments show that phosphinic acid does not promote S(N)1 reactivity. Density functional theory calculations corroborate a reaction pathway where the phosphinic acid operates as a bifunctional catalyst in the intramolecular substitution reaction. In this mechanism, the acidic proton of the phosphinic acid protonates the hydroxyl group, enhancing the leaving group ability. Simultaneously, the oxo group of phosphinic acid operates as a base abstracting the nucleophilic proton and thus enhancing the nucleophilicity. This reaction will open up new atom efficient techniques that enable alcohols to be used as nucleofuges in substitution reactions in the future.

  • 3.
    Bunrit, Anon
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Dahlstrand, Christian
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Srifa, Pemikar
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Olsson, Sandra K.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Huang, Genping
    Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden.;Tianjin Univ, Sch Sci, Dept Chem, Tianjin 300072, Peoples R China..
    Biswas, Srijit
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC. Ctr Biomed Res, Lucknow 226014, Uttar Pradesh, India..
    Himo, Fahmi
    Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden..
    Samec, Joseph S. M.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC. Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden..
    Nucleophilic Substitution of the Hydroxyl Group in Stereogenic Alcohols with Chirality Transfer2016In: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, Vol. 27, no 2, p. 173-176Article in journal (Refereed)
    Abstract [en]

    A brief overview of the development of direct substitution of the hydroxyl (OH) group of alcohols in our research group is presented. By applying a BrOnsted acid, an intramolecular substitution of the OH group in stereogenic alcohols with chirality transfer was achieved. Noteworthy, the intramolecular substitution has a wide scope in respect to both the nucleophile and also the nucleofuge. A mechanistic study by both experiments and DFT calculations revealed a unique reaction pathway in which the BrOnsted acid operates in a bifunctional manner to promote an S(N)2-type reaction mechanism.

  • 4.
    Bunrit, Anon
    et al.
    Stockholm Univ, Organ Chem, Stockholm, Sweden..
    Watile, Rahul
    Stockholm Univ, Organ Chem, Stockholm, Sweden..
    Dahlstrand, Christian
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Olsson, Sandra
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Srifa, Pemikar
    Stockholm Univ, Organ Chem, Stockholm, Sweden..
    Huang, Genping
    Stockholm Univ, Organ Chem, Stockholm, Sweden..
    Biswas, Srijit
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Himo, Fahmi
    Stockholm Univ, Organ Chem, Stockholm, Sweden..
    Samec, Joseph
    Stockholm Univ, Organ Chem, Stockholm, Sweden..
    H3PO2-catalyzed intramolecular stereospecific nucleophilic substitution of the hydroxyl group in stereogenic alcohols2017In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 254Article in journal (Other academic)
  • 5.
    Olsson, Sandra
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Host-Guest Interactions for Structural Analysis of Organic Molecules: Development of new Tools for Stereochemical Characterization2019Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The focus of this thesis is on the development of molecular tweezers as host-guest systems for stereochemical characterization of small organic molecules.

    There are two central problems to stereochemical characterization of small molecules. The first is that there are few methods for the determination of absolute stereochemistry and the complexity of the task increases with the number of chiral centres in the molecule. The second is the flexibility of small molecules. The data received from NMR spectroscopy, the standard method for structural characterization is an average of all conformers present in solution, making exact determination of the structure challenging if stereocenters are involved.

    This research group has previously developed two bis-porphyrin molecular tweezers that can be used as hosts for relative stereochemical determination by NMR (NAMFIS) by limiting the flexibility of the guest molecules and for absolute stereochemical determination Exciton-Coupled Circular Dichroism (ECCD) by providing suitable chromophores. However, the use of these tweezers was limited to diamine molecules.

    To extend the application of both tweezer host systems, a range of metalloporphyrins have been investigated both computationally and experimentally to identify candidates binding strongly to oxygen containing functional groups (Paper I). One of the porphyrins identified has been used to synthesise a new system with the potential to be used for relative stereochemical determination by NMR (NAMFIS) of molecules with a wide variety of functional groups (Paper IV).

    To further develop the systems, the photo-isomerization properties of the stiff stilbene linker of one of the tweezers has been investigated. Macrocyclic diether model compounds, incorporating the stiff stilbene linker have been used to show that the photo-isomerizability strongly is affected by molecular strain (Paper II). The results suggest that if paired with a suitable porphyrin (with no UV/Vis absorption overlap) a photo-switchable tweezer might be constructed.

    To map the guest range of the stiff stilbene linked tweezer it was found that this tweezer gives strong to moderate signals for monoamines with a rigid structure (Paper III). As ditopic binding is usually a requirement for an ECCD signal when using bis-porphyrin molecular tweezers, this is a discovery that should be of general interest.

    List of papers
    1. Design of oxophilic metalloporphyrins: an experimental and DFT study of methanol binding
    Open this publication in new window or tab >>Design of oxophilic metalloporphyrins: an experimental and DFT study of methanol binding
    2018 (English)In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 47, no 33, p. 11572-11585Article in journal (Refereed) Published
    Abstract [en]

    By systematic measurements we have evaluated a series of tetraphenyl metalloporphyrins and halogenated tetraphenyl metalloporphyrin derivatives for binding to ligands with oxygen containing functional groups, using methanol, acetic acid and acetone as examples. Experimental binding constants identified three metalloporphyrins with good binding to all three ligands: MgTPFPP, MgTPPBr8 and ZnTPPBr8 as well as a range of porphyrins binding to select ligands. Based on these results the optimal porphyrins can be selected for the desired binding interactions. We also show how to use DFT calculations to evaluate the potential binding between a metalloporphyrin and a ligand, which is deduced from free energies of binding ΔG, charge transfer ΔQ, and change of metal spin state. Computations on unsubstituted porphyrins in lieu of tetraphenyl porphyrin systems yield reliable predictions of binding interactions with good correlation to the corresponding experimental data. The calculations have also yielded interesting insights into the effect of halogenation in the β-position on the binding to ligands with oxygen containing functional groups.

    Place, publisher, year, edition, pages
    Royal Society of Chemistry, 2018
    Keywords
    Porphyrins, DFT, host-guest
    National Category
    Organic Chemistry
    Research subject
    Chemistry with specialization in Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-359830 (URN)10.1039/c8dt02432d (DOI)000442509700031 ()30087966 (PubMedID)
    Funder
    Swedish Research Council, 621-2012-3379Carl Tryggers foundation , 16:156Swedish National Infrastructure for Computing (SNIC), 2018/3-240National Supercomputer Centre (NSC), Sweden, SNIC 2018/3-240
    Available from: 2018-09-06 Created: 2018-09-06 Last updated: 2019-04-23Bibliographically approved
    2. Effect of Ring Size on Photoisomerization Properties of Stiff Stilbene macrocycles
    Open this publication in new window or tab >>Effect of Ring Size on Photoisomerization Properties of Stiff Stilbene macrocycles
    (English)Manuscript (preprint) (Other academic)
    Abstract [en]

    A series of stiff stilbene macrocycles have been studied in order to investigate the possible impact of macrocycle ring size on their photo-dynamic properties. The results show that reducing the ring size counteracts the photoisomerization ability of the macrocycles. However, even the smallest macrocycle studied (stiff stilbene subunits linked by a six carbon chain) showed some degree of isomerization when irradiated. DFT calculations of the energy differences between the E- and Z-isomers show the same trend as the experimental results. Interestingly the DFT study highlights that the energy difference between the E- and Z-isomers of even the largest macrocycle (linked by a twelve carbon chain) is significantly higher than that of the stiff stilbene unit itself. This indicates that a flexible chain may significantly affect the efficiency of photoisomerizations.

    Keywords
    Stiff stilbene cyclic photoisomerization
    National Category
    Organic Chemistry
    Research subject
    Chemistry with specialization in Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-382215 (URN)
    Funder
    Swedish Research Council, 621-2012-3379Carl Tryggers foundation , CTS 16:156Swedish National Infrastructure for Computing (SNIC)
    Available from: 2019-04-23 Created: 2019-04-23 Last updated: 2019-04-23
    3. Exciton-Coupled Circular Dichroism Characterization of Monotopically Binding Guests in Host-Guest Complexes with a Bis(zinc porphyrin) Tweezer
    Open this publication in new window or tab >>Exciton-Coupled Circular Dichroism Characterization of Monotopically Binding Guests in Host-Guest Complexes with a Bis(zinc porphyrin) Tweezer
    2018 (English)In: ChemPlusChem, ISSN 2192-6506, Vol. 83, p. 1169-1178Article in journal (Refereed) Published
    Abstract [en]

    A stiff-stilbene-linked bisporphyrin tweezer with inherent helicity was used for exciton-coupled circular dichroism (ECCD) characterization of a series of monotopically binding amine guest molecules. CD signals were observed for a variety of monoamines at relatively low tweezer/amine (host/guest) ratios between 1 :10 to 1: 70. For the amines producing the most intense CD signals, a binding stoichiometry of 1:2 was found. A likely explanation is the presence of guest-guest interactions in the complexes. This is supported by the correlation observed between CD signal intensity and magnitude of possible noncovalent binding between the guests, which can be divided into three groups showing no, moderate and strong response, respectively. Further support for this rationalization comes from molecular modelling.

    Place, publisher, year, edition, pages
    Weinheim: Wiley-VCH Verlagsgesellschaft, 2018
    Keywords
    bis-porphyrin tweezers, conformation analysis, exciton-coupled circular dichroism, host-guest systems, molecular modeling
    National Category
    Organic Chemistry
    Research subject
    Chemistry with specialization in Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-371629 (URN)10.1002/cplu.201800564 (DOI)000454527200013 ()
    Funder
    Swedish Research Council, 621-2012-3379Carl Tryggers foundation , CTS 16 : 156
    Available from: 2018-12-21 Created: 2018-12-21 Last updated: 2019-04-23Bibliographically approved
    4. Synthesis of a novel bis-Mg-porphyrin tweezer
    Open this publication in new window or tab >>Synthesis of a novel bis-Mg-porphyrin tweezer
    (English)Manuscript (preprint) (Other academic)
    Abstract [en]

    We have synthesised a novel semi-rigid bis-(magnesium-porphyrin) tweezer with a glycoluril backbone. meso-Tetrakis(pentafluorophenyl)porphyrin constitutes the two porphyrin units, each holding a magnesium(II) ion, and being connected to the glycoluril backbone via two -positions. This connection prevents any porphyrin rotation, leaving changes in gap size as sole conformational variation. Magnesium(II) tetrakis(pentafluorophenyl)porphyrin has in previous studies shown to bind well to both nitrogen-containing and oxygen-containing functional groups. The tweezer has the potential to retain this binding ability, which would be useful in the stereochemical characterization of small flexible molecules with multiple stereocentra and a wide variety of functional groups.

    Keywords
    magnesium-porphyrin tweezer synthesis
    National Category
    Organic Chemistry
    Research subject
    Chemistry with specialization in Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-382217 (URN)
    Funder
    Swedish Research Council, 621-2012-3379Carl Tryggers foundation , CTS 16:156
    Available from: 2019-04-23 Created: 2019-04-23 Last updated: 2019-04-23
  • 6.
    Olsson, Sandra K.
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
    Benito Perez, Oscar
    Universitat de Barcelona.
    Blom, Magnus
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
    Effect of Ring Size on Photoisomerization Properties of Stiff Stilbene macrocyclesManuscript (preprint) (Other academic)
    Abstract [en]

    A series of stiff stilbene macrocycles have been studied in order to investigate the possible impact of macrocycle ring size on their photo-dynamic properties. The results show that reducing the ring size counteracts the photoisomerization ability of the macrocycles. However, even the smallest macrocycle studied (stiff stilbene subunits linked by a six carbon chain) showed some degree of isomerization when irradiated. DFT calculations of the energy differences between the E- and Z-isomers show the same trend as the experimental results. Interestingly the DFT study highlights that the energy difference between the E- and Z-isomers of even the largest macrocycle (linked by a twelve carbon chain) is significantly higher than that of the stiff stilbene unit itself. This indicates that a flexible chain may significantly affect the efficiency of photoisomerizations.

  • 7.
    Olsson, Sandra K.
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
    Dahlstrand, Christian
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
    Design of oxophilic metalloporphyrins: an experimental and DFT study of methanol binding2018In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 47, no 33, p. 11572-11585Article in journal (Refereed)
    Abstract [en]

    By systematic measurements we have evaluated a series of tetraphenyl metalloporphyrins and halogenated tetraphenyl metalloporphyrin derivatives for binding to ligands with oxygen containing functional groups, using methanol, acetic acid and acetone as examples. Experimental binding constants identified three metalloporphyrins with good binding to all three ligands: MgTPFPP, MgTPPBr8 and ZnTPPBr8 as well as a range of porphyrins binding to select ligands. Based on these results the optimal porphyrins can be selected for the desired binding interactions. We also show how to use DFT calculations to evaluate the potential binding between a metalloporphyrin and a ligand, which is deduced from free energies of binding ΔG, charge transfer ΔQ, and change of metal spin state. Computations on unsubstituted porphyrins in lieu of tetraphenyl porphyrin systems yield reliable predictions of binding interactions with good correlation to the corresponding experimental data. The calculations have also yielded interesting insights into the effect of halogenation in the β-position on the binding to ligands with oxygen containing functional groups.

  • 8.
    Olsson, Sandra K.
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
    Synthesis of a novel bis-Mg-porphyrin tweezerManuscript (preprint) (Other academic)
    Abstract [en]

    We have synthesised a novel semi-rigid bis-(magnesium-porphyrin) tweezer with a glycoluril backbone. meso-Tetrakis(pentafluorophenyl)porphyrin constitutes the two porphyrin units, each holding a magnesium(II) ion, and being connected to the glycoluril backbone via two -positions. This connection prevents any porphyrin rotation, leaving changes in gap size as sole conformational variation. Magnesium(II) tetrakis(pentafluorophenyl)porphyrin has in previous studies shown to bind well to both nitrogen-containing and oxygen-containing functional groups. The tweezer has the potential to retain this binding ability, which would be useful in the stereochemical characterization of small flexible molecules with multiple stereocentra and a wide variety of functional groups.

  • 9.
    Olsson, Sandra K.
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
    Schäfer, Clara
    Friedrich-Alexander-University Erlangen-Nürnberg.
    Blom, Magnus
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
    Exciton-Coupled Circular Dichroism Characterization of Monotopically Binding Guests in Host-Guest Complexes with a Bis(zinc porphyrin) Tweezer2018In: ChemPlusChem, ISSN 2192-6506, Vol. 83, p. 1169-1178Article in journal (Refereed)
    Abstract [en]

    A stiff-stilbene-linked bisporphyrin tweezer with inherent helicity was used for exciton-coupled circular dichroism (ECCD) characterization of a series of monotopically binding amine guest molecules. CD signals were observed for a variety of monoamines at relatively low tweezer/amine (host/guest) ratios between 1 :10 to 1: 70. For the amines producing the most intense CD signals, a binding stoichiometry of 1:2 was found. A likely explanation is the presence of guest-guest interactions in the complexes. This is supported by the correlation observed between CD signal intensity and magnitude of possible noncovalent binding between the guests, which can be divided into three groups showing no, moderate and strong response, respectively. Further support for this rationalization comes from molecular modelling.

1 - 9 of 9
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