Bulk Inclusions of Pyridazine-Based Molecular Rotors in Tris(o-phenylenedioxy)cyclotriphosphazene (TPP)
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F16%3A00466267" target="_blank" >RIV/61388963:_____/16:00466267 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/adfm.201600437" target="_blank" >http://dx.doi.org/10.1002/adfm.201600437</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/adfm.201600437" target="_blank" >10.1002/adfm.201600437</a>
Alternative languages
Result language
angličtina
Original language name
Bulk Inclusions of Pyridazine-Based Molecular Rotors in Tris(o-phenylenedioxy)cyclotriphosphazene (TPP)
Original language description
A new class of rod-shaped strongly dipolar molecular rotors for insertion into channels of hexagonal tris(o-phenylenedioxy)cyclotriphosphazene (TPP) has been examined. Seven different 3,6-disubstituted pyridazines and one singly 3-substituted system have been prepared and studied by solid-state nuclear magnetic resonance (NMR), X-ray powder diffraction, and dielectric spectroscopy. NMR and X-ray diffraction both show that all but one of these molecular rotors form hexagonal bulk inclusion compounds with TPP. In-plane lattice parameters for the hexagonal phases increase with the size of the end group, which also controls the energy barriers for rotation of the pyridazine dipole. The barriers range from approximate to 4 kcal mol(-1) for small or flexible end groups to less than 0.7 kcal mol(-1) for 3-methylbicyclo[1.1.1]pent-1-yl end groups after annealing to 235 degrees C, and an interpretation of these differences is offered. Computer modeling of the relaxed TPP channels followed by density functional calculation of the environment for one of the rotors provides quantitative agreement with the observed barrier. The systems with the lowest rotational barriers show signs of collective behavior, discussed in terms of antiferroelectric intrachannel and ferroelectric interchannel dipole-dipole interactions. A Curie temperature of 22 K is deduced for 3,6-diadamant-1-ylpyridazine, but no ordered dielectric phases are found. Conclusions have been drawn for improved rotor design.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Advanced Functional Materials
ISSN
1616-301X
e-ISSN
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Volume of the periodical
26
Issue of the periodical within the volume
31
Country of publishing house
DE - GERMANY
Number of pages
15
Pages from-to
5718-5732
UT code for WoS article
000383568300013
EID of the result in the Scopus database
2-s2.0-84971613803