Figure - available from: Zeitschrift für Kristallographie. New crystal structures
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PL spectra of 1,8-bis(p-tolylthio)pyrene in DCM in the presence of different content of m-chloroperoxybenzoic acid from 0 to 3 eq. For PL measurement, 1,8-bis(p-tolylthio)pyrene concentration: 10⁻⁵ M, excitation wavelength: 365 nm.
Source publication
C 30 H 22 S 2 , triclinic, P 1̄ (no. 2), a = 7.604(4) Å, b = 11.556(5) Å, c = 13.090(7) Å, α = 93.964(8)°, β = 93.209(8)°, γ = 90.619(9)°, V = 1145.7(10) Å ³ , Z = 2, Rgt ( F ) = 0.0497, wRref ( F² ) = 0.1295, T = 296(2) K.
Similar publications
C 18 H 14 S 2 , monoclinic, P 2 1 / c (no. 14), a = 10.196(3) Å, b = 14.756(4) Å, c = 9.508(3) Å, β = 103.965(14)°, V = 1388.3(7) Å ³ , Z = 4, Rgt ( F ) = 0.0480, wRref ( F² ) = 0.1207, T = 200(2) K.
C30H22S2, triclinic, P1‾$P‾{1}$ (no. 2), a = 7.5621(2) Å, b = 8.6787(3) Å, c = 9.8951(3) Å, α = 110.4180(10)°, β = 97.6810(10)°, γ = 108.8430(10)°, V = 553.33(3) Å3, Z = 1, R
gt(F) = 0.0413, wR
ref(F
2) = 0.1160, T = 200(2) K.
Citations
... Generally, the 1-, 3-, 6-and 8-positions of pyrene core preferentially undergo electrophilic aromatic substitution reactions. Thus, various 1-substi tuted pyrenes, 1,6-disubstituted, 1,8-disubstituted and 1,3,6,8-tetrasubstituted pyrenes with same group can be easily obtained [18,[20][21][22][23]. There are very limited studies on 2-or 4-substituted pyrene because the position is not directly accessible by electrophilic substitution of pyrene itself, and only a few 2-or 4-substituted pyrenes have been obtained up to date [24,25]. ...
C18H12O, triclinic, P1‾ (no. 2), a = 10.132(2) Å, b = 10.654(2) Å, c = 11.730(2) Å, α = 90.31(3)°, β = 102.38(3)°, γ = 104.81(3)°, V = 1193.2(4) Å3, Z = 4, Rgt(F) = 0.0403, wRref(F2) = 0.1037, T = 293(2) K.
... The intermediate 1,6-dibromopyrene was prepared through the bromination of pyrene according to the literature [4]. The title compound was synthesized according to the similar method in the literature [5] and the detailed procedures were displayed as following: Firstly, 3.38 g (24 mmol) of p-methylthiophenol, 3.60 g (10 mmol) of 1,6-dibromopyrene and 80 mL of dimethylformamide (DMF) were added to a 150 mL round bottom flask. The resulting mixture was stirred for 20 min in an ice bath under the protection of nitrogen atmosphere. ...
... Organic functional molecules with tunable optical, biological and bifunctional as well as mutifunctional properties have gained great deal of attention due to their potential applications in sensors, live-cell imaging, organic solar cells (OSCs), organic light-emitting diodes (OLEDs) and so on [5][6][7][8][9][10][11]. As one of the most well-known functional molecules, pyrene and its derivatives have been widely investigated by many researchers because of their effectively fluorescent emission, facile synthesis and easy functionalization. ...
... Organic functional molecules containing sulfur atoms have also attracted extensive research interest because their special electronic structures may result into special properties, which could develop more novel functional material precursors. Very recently, the crystal structures of pyrene-based thioether compounds such as 1,3,6,8-tetrakis(p-tolylthio)pyrene, 1,8-bis(p-tolylthio)pyrene, 1,6-bis(methylthio)pyrene and so on, have been reported by our group using pyrene as the starting material [5,[19][20][21], especially, some of them exhibit relatively excellent fluorescent properties and sensor function for peroxides such as m-chloroperoxybenzoic acid. As a continuation of this work, herein, we report the crystal structure of a new pyrene-based thioether compound which was synthesized in high yield. ...
C30H22S2, triclinic, P1‾$P‾{1}$ (no. 2), a = 7.5621(2) Å, b = 8.6787(3) Å, c = 9.8951(3) Å, α = 110.4180(10)°, β = 97.6810(10)°, γ = 108.8430(10)°, V = 553.33(3) Å3, Z = 1, R
gt(F) = 0.0413, wR
ref(F
2) = 0.1160, T = 200(2) K.
... Compared with the reports on nitrogen-containing, pyrene-based compounds, the studies on pyrene-based thioether compounds are relatively limited. Recently, Xu and Wen et al. have reported the crystal structure of one diaryl sulfide 1,3,6,8-tetrakis(p-tolylthio)pyrene and 1,8bis(p-tolylthio)pyrene using pyrene as the starting precursor [16,17]. Herein, we report the crystal structure of a new pyrene-based arylalkyl thioether, 1,6-bis(methylthio)pyrene, which was synthesized by the nucleophilic substitution reaction of sodium thiomethoxide with 1,6-dibromopyrene in high yield. ...
... C9-S2-C18. The C-S bond distances and C-S-C bond angles are within the expected values for diaryl sulfide compounds and they are comparable to those found in 1,3,6,8-tetrakis(p-tolylthio)pyrene and 1,8-bis(p-tolylthio) pyrene [16,17]. The crystal packing of the title compound can be described by the analysis of three main intermolecular interactions. ...
... The crystal state emits yellow-green fluorescence with a peak at 530 nm. Similar to 1,8-bis(p-tolylthio)pyrene [17], the title compound also can be oxided by some peroxides such as m-chloroperoxybenzoic acid and displays "onoff" optical switching property. However, its sensitivity for m-chloroperoxybenzoic acid is significantly lower than that of 1,8-bis(p-tolylthio)pyrene, which may be due to the fact that the oxidation of alkylarylsulfide is difficult compared to diarylsulfide. ...
C 18 H 14 S 2 , monoclinic, P 2 1 / c (no. 14), a = 10.196(3) Å, b = 14.756(4) Å, c = 9.508(3) Å, β = 103.965(14)°, V = 1388.3(7) Å ³ , Z = 4, Rgt ( F ) = 0.0480, wRref ( F² ) = 0.1207, T = 200(2) K.
