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Arrays of Dipolar Molecular Rotors in Tris(o-phenylenedioxy)cyclotriphosphazene

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Molecular Machines and Motors

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 354))

Abstract

Regular two-dimensional or three-dimensional arrays of mutually interacting dipolar molecular rotors represent a worthy synthetic objective. Their dielectric properties, including possible collective behavior, will be a sensitive function of the location of the rotors, the orientation of their axes, and the size of their dipoles. Host–guest chemistry is one possible approach to gaining fine control over these factors. We describe the progress that has been achieved in recent years using tris(o-phenylenedioxy)cyclotriphosphazene as a host and a series of rod-shaped dipolar molecular rotors as guests. Structures of both surface and bulk inclusion compounds have been established primarily by solid-state nuclear magnetic resonance (NMR) and powder X-ray diffraction (XRD) techniques. Low-temperature dielectric spectroscopy revealed rotational barriers as low as 1.5 kcal/mol, but no definitive evidence for collective behavior has been obtained so far.

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Abbreviations

(ss)NMR:

(Solid-state) nuclear magnetic resonance

2-D:

Two-dimensional

3-D:

Three-dimensional

B97-D3/SVP//PM6:

Density functional theory calculation with the B97-D3 functional and SVP basis set at a geometry optimized with the PM6 method

Boc:

tert-Butoxycarbonyl

Bu:

n-Butyl

CP MAS:

Cross-polarization with magic angle spinning

DMF:

Dimethylformamide

DSC:

Differential scanning calorimetry

Et:

Ethyl

Hex:

n-Hexyl

Me:

Methyl

TBACl:

Tetra(n-butyl)ammonium chloride

TBAF:

Tetra(n-butyl)ammonium fluoride

THF:

Tetrahydrofuran

TIPS:

Tris(isopropyl)silyl

TMS:

Trimethylsilyl

TMSA:

Trimethylsilylacetylene

TPP:

Tris(o-phenylenedioxy)cyclotriphosphazene

Ts:

p-Toluenesulfonyl

Xmol%Y@TPP:

Inclusion compound containing X% of guest Y in TPP as host

XRD:

Powder X-ray diffraction

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Acknowledgement

This material is based upon work supported in Prague by the European Research Council under the European Community’s Seventh Framework Programme (FP7/2007–2013) ERC grant agreement no. 227756 and by the Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic RVO: 61388963, and in Boulder by the National Science Foundation under Grant No. CHE 0848663. We are grateful to Dr. Martina Čižková for taking the TEM image shown in Fig. 5.

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Authors and Affiliations

  1. Department of Physics, University of Colorado, Boulder, CO, 80309, USA

    Ke Zhao & Charles T. Rogers

  2. Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO, 80309, USA

    Paul I. Dron & Josef Michl

  3. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 16610, Prague 6, Czech Republic

    Jiří Kaleta & Josef Michl

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  1. Ke Zhao
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  2. Paul I. Dron
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  3. Jiří Kaleta
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  5. Josef Michl
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Correspondence to Josef Michl .

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Editors and Affiliations

  1. Dept. of Chemistry “Giacomo Ciamician”, University of Bologna, Bologna, Italy

    Alberto Credi

  2. Dept. of Chemistry “Giacomo Ciamician”, University of Bologna, Bologna, Germany

    Serena Silvi

  3. Dept. of Chemistry “Giacomo Ciamician", University of Bologna, Bologna, Italy

    Margherita Venturi

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Zhao, K., Dron, P.I., Kaleta, J., Rogers, C.T., Michl, J. (2014). Arrays of Dipolar Molecular Rotors in Tris(o-phenylenedioxy)cyclotriphosphazene. In: Credi, A., Silvi, S., Venturi, M. (eds) Molecular Machines and Motors. Topics in Current Chemistry, vol 354. Springer, Cham. https://doi.org/10.1007/128_2013_513

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