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Organic binary charge-transfer compounds of 2,2′ : 6′,2′′ : 6′′,6-trioxotriphenylamine and a pyrene-annulated azaacene as donors
Three binary charge-transfer (CT) compounds resulting from the donor 2,2′ : 6′,2′′ : 6′′,6-trioxotriphenylamine (TOTA) and the acceptors F 4 TCNQ and F 4 BQ and of a pyrene-annulated azaacene (PAA) with the acceptor F 4 TCNQ are reported. The identity of these CT compounds are confirmed by single-cr...
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Published in: | RSC advances 2023-01, Vol.13 (6), p.3652-366 |
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Main Authors: | , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | Three binary charge-transfer (CT) compounds resulting from the donor 2,2′ : 6′,2′′ : 6′′,6-trioxotriphenylamine (TOTA) and the acceptors F
4
TCNQ and F
4
BQ and of a pyrene-annulated azaacene (PAA) with the acceptor F
4
TCNQ are reported. The identity of these CT compounds are confirmed by single-crystal X-ray diffraction as well as by IR, UV-vis-NIR and EPR spectroscopy. X-ray diffraction analysis reveals a 1 : 1 stoichiometry for TOTA·F
4
TCNQ, a 2 : 1 donor : acceptor ratio in (TOTA)
2
·F
4
BQ, and a rare 4 : 1 stoichiometry in (PAA)
4
·F
4
TCNQ, respectively. Metrical parameters of the donor (D) and acceptor (A) constituents as well as IR spectra indicate full CT in TOTA·F
4
TCNQ, partial CT in (TOTA)
2
·F
4
BQ and only a very modest one in (PAA)
4
·F
4
TCNQ. Intricate packing motifs are present in the crystal lattice with encaged, π-stacked (F
4
TCNQ
−
)
2
dimers in TOTA·F
4
TCNQ or mixed D/A stacks in the other two compounds. Their solid-state UV-vis-NIR spectra feature CT transitions. The CT compounds with F
4
TCNQ are electrical insulators, while (TOTA)
2
·F
4
BQ is weakly conducting.
Three binary charge-transfer (CT) compounds resulting from the donor 2,2′ : 6′,2′′ : 6′′,6-trioxotriphenylamine (TOTA) and the acceptors F
4
TCNQ and F
4
BQ and of a pyrene-annulated azaacene (PAA) with the acceptor F
4
TCNQ are reported. |
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ISSN: | 2046-2069 2046-2069 |
DOI: | 10.1039/d2ra07322f |