Dielectric response of 1,1-difluorosumanene caused by an in-plane motion

Abstract

We have designed and synthesized a new curved π-conjugated molecule, 1,1-difluorosumanene (1), which possesses two fluorine atoms on the same benzylic carbon of unsubstituted sumanene, producing a large dipole moment...

Tuning the dielectric response by co-crystallisation of sumanene and its fluorinated derivative

“…S6, ESI †). 19 The variable-temperature powder X-ray diffraction (VT-PXRD) analysis of these co-crystals gave more detailed insights into the thermal behaviour of the co-crystals (Fig. S7, ESI †).…”

“…1b). 19 This phenomenon showed an anisotropic Debye-type dielectric response under an electric field due to the presence of a strong dipole induced by the fluorine introduction. Noteworthy is that all reported fluorosumanenes, F2-Sum and hexafluorosumanene F6-Sum , give the isostructural hexagonal packing pattern to Sum with the R 3 c space group.…”

“…Both the Table 1 Structural parameters of Sum, F2-Sum, and F6-Sum. All the parameters were based on single-crystal X-ray analysis data at 100 K. 16,19,20 Bowl depth is the vertical distance from the peripheral aromatic carbon to the plane in which the bottom hexagonal ring forms. The definitions of bowl-tobowl distance and intercolumnar distance are shown in the figure below the table…”

Molecular-Shape-Organized Stimuli-Responsive Functional Crystalline Systems

“…Before starting the project, we were reminded that previously reported 1,1,4,4,7,7─ hexa uorosumanene (6), which contains two uorine atoms on each of the three benzylic carbons, affords a crystal that is isostructural to that of 3, 45 indicating that the introduction of uorine atom onto the sumanene skeleton does not signi cantly affect its packing pattern. Because of this feature and the large electronegativity of uorine atoms, we chose to synthesize 1,1─ di uorosumanene (5), which contains two uorine atoms on one of the benzylic carbons of 3 and we investigated the motions of this compound 46 in relation to its dielectric response. 47─ 50 1,1─ Di uorosumanene (5) was synthesized by a modi ed form of a reported procedure (Scheme 3).…”

Sumanene-functionalised bis(terpyridine)–ruthenium(ii) complexes showing photoinduced structural change and cation sensing

“…21 This structural feature has been the source of the emergence of unique physical properties of various kinds of sumanene derivatives. [22][23][24][25][26][27] In addition, it is worth noting that sumanene shows a metal cation trapping ability. In the early stage, Sastry et al systematically explored Li + , Na + , K + and Cu + complexes of sumanene in terms of the formation of cation-π interactions by employing ab initio quantum mechanical tools.…”