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Title: Host-Guest Complexes of Cyclodextrins and Nanodiamonds as a Strong Non-Covalent Binding Motif for Self-Assembled Nanomaterials

Authors:
 [1]; ORCiD logo [2];  [3]; ORCiD logo [4];  [3]; ORCiD logo [1]
  1. Organic Chemistry Institute and CeNTech, Westfälische Wilhelms-Universität Münster, Corrensstr.40 48149 Münster Germany
  2. Organic Chemistry Institute and CeNTech, Westfälische Wilhelms-Universität Münster, Corrensstr.40 48149 Münster Germany, Current address: Institute of Organic Chemistry, University of Duisburg-Essen, Universitätsstraße 7 45141 Essen Germany
  3. Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 17 35392 Giessen Germany
  4. Stanford Institute for Materials and Energy Science, SLAC National Accelerator Laboratory, 2575 Sand Hill Road Menlo Park CA 94025 USA
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1407823
Resource Type:
Journal Article: Publisher's Accepted Manuscript
Journal Name:
Chemistry - A European Journal
Additional Journal Information:
Journal Volume: 23; Journal Issue: 63; Related Information: CHORUS Timestamp: 2017-11-13 02:54:22; Journal ID: ISSN 0947-6539
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

Schibilla, Frauke, Voskuhl, Jens, Fokina, Natalie A., Dahl, Jeremy E. P., Schreiner, Peter R., and Ravoo, Bart Jan. Host-Guest Complexes of Cyclodextrins and Nanodiamonds as a Strong Non-Covalent Binding Motif for Self-Assembled Nanomaterials. Germany: N. p., 2017. Web. doi:10.1002/chem.201703392.
Schibilla, Frauke, Voskuhl, Jens, Fokina, Natalie A., Dahl, Jeremy E. P., Schreiner, Peter R., & Ravoo, Bart Jan. Host-Guest Complexes of Cyclodextrins and Nanodiamonds as a Strong Non-Covalent Binding Motif for Self-Assembled Nanomaterials. Germany. doi:10.1002/chem.201703392.
Schibilla, Frauke, Voskuhl, Jens, Fokina, Natalie A., Dahl, Jeremy E. P., Schreiner, Peter R., and Ravoo, Bart Jan. 2017. "Host-Guest Complexes of Cyclodextrins and Nanodiamonds as a Strong Non-Covalent Binding Motif for Self-Assembled Nanomaterials". Germany. doi:10.1002/chem.201703392.
@article{osti_1407823,
title = {Host-Guest Complexes of Cyclodextrins and Nanodiamonds as a Strong Non-Covalent Binding Motif for Self-Assembled Nanomaterials},
author = {Schibilla, Frauke and Voskuhl, Jens and Fokina, Natalie A. and Dahl, Jeremy E. P. and Schreiner, Peter R. and Ravoo, Bart Jan},
abstractNote = {},
doi = {10.1002/chem.201703392},
journal = {Chemistry - A European Journal},
number = 63,
volume = 23,
place = {Germany},
year = 2017,
month =
}

Journal Article:
Free Publicly Available Full Text
This content will become publicly available on November 6, 2018
Publisher's Accepted Manuscript

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  • Transient ternary complexes of the general form metalloporphyrin-DABCO-metalloporphyrin are described and characterized by NMR spectroscopy: the protons of DABCO (1,4-diazobicyclo(2.2.2)octane) molecules sandwiched between two diamagnetic metalloporphyrins resonate around {minus}5 ppm. The same structural motif is shown to occur when DABCO binds within the cavity of cofacial metalloporphyrin dimers. The kinetics and thermodynamics of intracavity binding were measured by electronic and NMR spectroscopy and lead to an estimate of 48 {plus minus} 10 kJ mol{sup {minus}1} (11.5 {plus minus} 2.4 kcal mol{sup {minus}1}) for the enthalpy of the {pi}-{pi} interaction between two zinc porphyrin moieties. The mechanism of ligand exchange andmore » isomer interconversion for one of the porphyrin dimers has also been elucidated.« less
  • We report here our results for Langmuir monolayers of the derivatives of cyclodextrin shown: hexakis(6-deoxy-6-dodecylamino)-{alpha}-cyclodextrin (1a), heptakis(6-deoxy-6-dodecylamino)-{beta}-cyclodextrin (1b), and heptakis(6-deoxy-6-dodecylthio)-{beta}-cyclodextrin (2b ), which was found to be partially substituted. Langmuir films of these derivatives were examined using {Pi}-A isotherm measurements and Brewster angle microscopy. Langmuir-Blodgett (LB) multilayer films of these derivatives were deposited from subphases containing p-nitrophenol to determine the extent of incorporation of the guest molecule in the LB film. The transfer ratios of the film exhibited a noteworthy evolution with the transfer pressure. The variation in the extent of guest molecule incorporation is discussed and compared with themore » binding behavior in solution of unmodified cyclodextrins. 29 refs., 4 figs.« less
  • NMR, UV-vis and isothermal titration calorimetry (ITC) measurements probe different aspects of competing host-guest equilibria as simple alkylammonium guest molecules interact with both the exterior (ion-association) and interior (encapsulation) of the [Ga{sub 4}L{sub 6}]{sup 12-} supramolecular assembly in water. Data obtained by each independent technique measure different components of the host-guest equilibria and only when analyzed together does a complete picture of the solution thermodynamics emerge. Striking differences between the internal and external guest binding are found. External binding is enthalpy driven and mainly due to attractive interactions between the guests and the exterior surface of the assembly while encapsulationmore » is entropy driven as a result of desolvation and release of solvent molecules from the host cavity.« less
  • Cyclic porphyrin trimers were synthesized through one-step cyclooligomerization via alkyne metathesis from diyne monomers. These macrocycles show interesting host-guest binding interactions with fullerenes, selectively binding C70 (6 x 103 M-1) over C60 and C84 (no binding observed). The fullerene-encapsulated host-guest complex can undergo guest or host exchange in the presence of another guest (2,4,6-tri(4-pyridyl)-1,3,5-triazine) or host (cage COP5) molecule with higher binding affinity.