Dithio-derivatives of p-quinodimethanes fused with 1,2,5-thiadiazoles: a novel type of π-donor–acceptor system

Yamashita, Yoshiro; Ono, Katsuhiko; Tanaka, Shoji; Imaeda, Kenichi; Inokuchi, Hiroo; Sano, Mizuka

doi:10.1039/c39930001803

Cited by 10 publications

(4 citation statements)

References 6 publications

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“…The arrangement of these heterocycles is especially attractive as it leaves room for pendant functional groups. A survey of the Cambridge Structural Database (CSD) , was performed to identify those crystals where these features are observed. ,,− This provided the average SBI distances that are compared in Table to the sum of the corresponding van der Waals radii. The two sets of data follow opposite trends, suggesting that the tellurium SBIs are the strongest.…”

Section: Resultsmentioning

confidence: 99%

The Nature of the Supramolecular Association of 1,2,5-Chalcogenadiazoles

et al. 2005

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Organochalcogen-nitrogen heterocycles such as the 1,2,5-chalcogenadiazoles have a distinct tendency to establish intermolecular links in the solid state through secondary bonding interactions E...N (E = S, Se, Te). The association of these molecules was examined in detail using relativistic density functional theory. Although there is an important electrostatic component, the interaction between these molecules is dominated by contributions arising from orbital mixing, which can be interpreted as the donation of a nitrogen lone pair into the chalcogen-centered antibonding orbitals. Because of its more polar character and lower-lying antibonding orbitals, the tellurium derivatives possess the strongest association energies; these are so large that the binding strength is comparable to that of some hydrogen bonds. In the absence of steric constraints, telluradiazoles associate in a coplanar fashion forming ribbon polymers. However, bulky susbstituents could be used to direct the formation of either helical chains or discrete dimers. In addition to its strength, the coplanar dimer is characterized by being rigid, yet no activation barrier is expected for the association/dissociation process. These attributes strongly indicate that tellurium-nitrogen heterocycles have great potential as building blocks in supramolecular architecture.

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Section: Resultsmentioning

confidence: 99%

The Nature of the Supramolecular Association of 1,2,5-Chalcogenadiazoles

et al. 2005

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“…The remainder of the table summarizes the properties of materials with less straightforward alternating donor-acceptor structures: copolymers containing both TDQ-and BT-containing monomers (67-69), 134 polymers containing platinum in the main chain (70,71), 135 and a small-molecules with electronwithdrawing substituents on the periphery (72). 136 Other more recent polymers incorporating dithienosilole 137 and benzodithiophene 138 donors showed similar results.…”

Section: Opvsmentioning

confidence: 90%

“…1), which forms single-component crystals that have high Hall charge-carrier mobility (3 cm 2 V À1 s À1 ). [69][70][71][72][73][74] In fact, the rst known isolated derivative of BBT was 4,8-bis(dicyanomethyl) derivative 11, which was obtained from two-electron reduction of BTDA-TCNQ and protonation of the stable, isolable disodium salt. 75 Indeed, in recent years the number of research articles on heteroannulated BT-containing materials has increased significantly, allowing an initial critical assessment of their properties and performance, which is the subject of this current review.…”

Section: Introductionmentioning

confidence: 99%

Heteroannulated acceptors based on benzothiadiazole

et al. 2015

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“…The chemical shift of proton H 4 of the dpq moiety is also significantly upfield-shifted (from 9.66 to 9.39 ppm for complexes 8 and 1, respectively) as a result of the establishment of intramolecular 1,5-sulfur-nitrogen interactions between the 1,3-dithiole and the pyrazine ring, as already described in the case of compound 4. 26 The 19 F spectrum of complex 1 exhibits characteristic peaks at -72.7 and -74.2 ppm for both PF 6 anions. MALDI-TOF results are in agreement with the structure of complex 1 with a molecular ion peak at m/z ) 1648 presenting an isotopic distribution in agreement with the calculated pattern.…”

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confidence: 97%