Startseite The crystal structure of 2,2′-(2,2-diphenylethene-1,1-diyl)bis(1,4-dimethoxybenzene), C30H28O4
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The crystal structure of 2,2′-(2,2-diphenylethene-1,1-diyl)bis(1,4-dimethoxybenzene), C30H28O4

  • Ya-Xuan Li , Jian-Qiao Li und Fei Zeng ORCID logo EMAIL logo
Veröffentlicht/Copyright: 23. Juli 2024

Abstract

C30H28O4, triclinic, P 1 (no. 2), a = 9.473(14) Å, b = 9.775(14) Å, c = 14.43(2) Å, α = 100.354(17)°, β = 91.053(17)°, γ = 94.062(17)°, V = 1310(1) Å3, Z = 2, R gt(F) = 0.0517, wR ref(F 2) = 0.1803, T = 296(2) K.

CCDC no.: 2358317

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colourless block
Size: 0.40 × 0.40 × 0.40 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 27.7°, 98 %
N(hkl)measured, N(hkl)unique, R int: 13,630, 5,562, 0.021
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 3,449
N(param)refined: 311
Programs: Bruker, 1 SHELX 2
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z U iso*/U eq
O1 0.11892 (16) 0.20842 (15) 0.15378 (10) 0.0884 (5)
O2 0.20897 (13) 0.72726 (14) 0.39574 (10) 0.0766 (4)
O3 0.56330 (13) 0.41804 (12) 0.31448 (8) 0.0654 (3)
O4 0.66003 (16) 0.92739 (13) 0.56554 (9) 0.0844 (4)
C1 0.2182 (3) 0.1652 (3) 0.08190 (18) 0.1082 (8)
H1A 0.229963 0.234497 0.042614 0.162*
H1B 0.182980 0.077919 0.044204 0.162*
H1C 0.307707 0.154518 0.110958 0.162*
C2 0.14620 (19) 0.33887 (19) 0.21215 (12) 0.0636 (5)
C3 0.04142 (19) 0.3805 (2) 0.27478 (13) 0.0718 (5)
H3 −0.040671 0.322575 0.275360 0.086*
C4 0.05751 (18) 0.5086 (2) 0.33718 (13) 0.0687 (5)
H4 −0.014150 0.535477 0.378254 0.082*
C5 0.18367 (17) 0.59799 (18) 0.33787 (12) 0.0566 (4)
C6 0.29186 (15) 0.55657 (17) 0.27501 (10) 0.0491 (4)
C7 0.27081 (17) 0.42688 (17) 0.21213 (11) 0.0550 (4)
H7 0.340830 0.399259 0.169914 0.066*
C8 0.1026 (2) 0.7754 (3) 0.46214 (16) 0.0938 (7)
H8A 0.017660 0.788138 0.428364 0.141*
H8B 0.136998 0.862447 0.500516 0.141*
H8C 0.082517 0.707525 0.501570 0.141*
C9 0.6208 (2) 0.29301 (19) 0.33198 (15) 0.0765 (5)
H9A 0.588648 0.216550 0.282930 0.115*
H9B 0.589864 0.273889 0.391670 0.115*
H9C 0.722301 0.304828 0.333052 0.115*
C10 0.59019 (16) 0.53893 (16) 0.38218 (10) 0.0478 (4)
C11 0.52516 (15) 0.65875 (16) 0.36359 (10) 0.0463 (4)
C12 0.55273 (17) 0.78517 (17) 0.42659 (10) 0.0532 (4)
H12 0.511011 0.864001 0.415017 0.064*
C13 0.64256 (18) 0.79571 (17) 0.50741 (11) 0.0573 (4)
C14 0.70382 (18) 0.67726 (18) 0.52588 (11) 0.0590 (4)
H14 0.761665 0.682814 0.579423 0.071*
C15 0.67782 (17) 0.54937 (17) 0.46325 (11) 0.0545 (4)
H15 0.719143 0.470772 0.475656 0.065*
C16 0.7404 (3) 0.9393 (2) 0.65257 (15) 0.1052 (9)
H16A 0.835791 0.916791 0.639220 0.158*
H16B 0.697972 0.875967 0.689619 0.158*
H16C 0.741002 1.033029 0.686968 0.158*
C17 0.43024 (15) 0.64684 (15) 0.27585 (10) 0.0457 (4)
C18 0.46991 (15) 0.70787 (15) 0.20068 (10) 0.0458 (4)
C19 0.37613 (16) 0.69912 (16) 0.11325 (10) 0.0500 (4)
C20 0.23297 (19) 0.7248 (2) 0.11748 (12) 0.0669 (5)
H20 0.193700 0.752956 0.175807 0.080*
C21 0.1477 (2) 0.7088 (2) 0.03554 (14) 0.0855 (6)
H21 0.052635 0.726556 0.039948 0.103*
C22 0.2044 (3) 0.6662 (2) −0.05337 (14) 0.0873 (7)
H22 0.146822 0.652885 −0.107634 0.105*
C23 0.3463 (2) 0.6444 (2) −0.05932 (13) 0.0808 (6)
H23 0.385214 0.618074 −0.117970 0.097*
C24 0.4323 (2) 0.66188 (19) 0.02278 (11) 0.0640 (5)
H24 0.528318 0.648690 0.017623 0.077*
C25 0.61532 (16) 0.78470 (16) 0.19834 (10) 0.0499 (4)
C26 0.74078 (18) 0.7247 (2) 0.21832 (12) 0.0646 (5)
H26 0.734858 0.635603 0.232827 0.078*
C27 0.8739 (2) 0.7957 (3) 0.21691 (15) 0.0823 (6)
H27 0.955040 0.754142 0.230935 0.099*
C28 0.8849 (2) 0.9295 (3) 0.19435 (15) 0.0886 (7)
H28 0.973294 0.977482 0.194593 0.106*
C29 0.7644 (3) 0.9902 (2) 0.17170 (14) 0.0812 (6)
H29 0.771835 1.078382 0.155617 0.097*
C30 0.6290 (2) 0.91769 (17) 0.17307 (13) 0.0677 (5)
H30 0.548408 0.958543 0.157071 0.081*

1 Source of material

A mixture of (2,5-dimethoxyphenyl)boronic acid (910 mg, 5.0 mmol), Na2CO3 (690 mg, 5.0 mmol) (2,2-dibromoethene-1,1-diyl)dibenzene (336 mg, 1.0 mmol) and tetrakis(triphenylphosphine)palladium (139 mg, 0.12 mmol) in 50 mL 1,4-dioxane/water (v/v = 4:1) in a flask was stirred at 90 °C for 24 h under N2. After evaporating the solvents, resulting mixture was extracted with dichloromethane (3 × 50 mL) and then washed with water and brine successively. The organic layer was dried over anhydrous Na2SO4 and removed in vacuo and the residue was separated by column chromatography on silica gel (eluent: 1:2 DCM/petroleum ether) to give the title compound (285 mg, yield 63 %) as yellow solid. Crystals of the title compound were obtained by slow vapour of solution of title compound in CH2Cl2 within 1 week.

2 Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

3 Comment

In 2001, Tang et al. reported a totally new class of organic fluorophore molecules, which are non-emissive or weakly emissive in solution but display strong fluorescence upon aggregation or in the solid state. 3 This novel photophysical phenomenon is coined the aggregation-induced emission (AIE) effect, and it steers clear of the notorious aggregation-caused quenching (ACQ) problem of conventional fluorophores in a solid emitter. 4 , 5 , 6 Tetraphenylethylene (TPE) is a simple small molecule with its π electrons in four phenyl rings delocalizing to the double bond. Due to the crowded phenyl substituents, the resultant repulsion makes the phenyl rings deviate from the π-π delocalization plane, resulting in a propeller-like arrangement. TPE derivatives have accounted for more than half of all AIEgen compounds, showing that they are the most quickly developed. 7 In 2001, Miller and coworkers reported the synthesis of 4,4′-(2,2-diphenylethene-1,1-diyl)bis(methoxybenzene) through the Suzuki reaction of (2,2-dibromoethene-1,1-diyl)dibenzene and (4-methoxyphenyl)boronic acid. 8 Bai and coworkers reported the preparation of 2,2′-(2,2-diphenylethene-1,1-diyl)bis(methoxybenzene) by the reaction between 2,2′-dimethyloxybenzophenone and the lithiated diphenylmethane at 70 °C for 24 h in THF, followed by dehydration in refluxing toluene with a Dean-Stark trap using p-toluenesulfonic acid as a catalyst. 9 Herein, we reported the synthesis of a new tetraphenylethylene derivative, which may enrich the tetraphenylethylene chemistry. The title compound, built up by the C30H28O4 molecules, has been synthesized. The single-crystal structure verifies that all bond lengths are in normal ranges.


Corresponding author: Fei Zeng, Department of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou, Hunan 425199, P.R. China, E-mail:

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Competing interest: The authors declare no conflicts of interest regarding this article.

  3. Research funding: The work was supported by General scientific research project of Hunan University of Science and Engineering.

References

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Received: 2024-05-26
Accepted: 2024-07-12
Published Online: 2024-07-23
Published in Print: 2024-10-28

© 2024 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

Artikel in diesem Heft

  1. Frontmatter
  2. Editorial
  3. Editorial 2024 – New developments and changes of Zeitschrift für Kristallographie – New Crystal Structures
  4. New Crystal Structures
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  6. The crystal structure of 6-amino-2-carboxypyridin-1-ium perchlorate, C6H7ClN2O6
  7. Crystal structure of poly[(μ4-(3-amino-1H-1,2,4-triazol-1-yl)benzene-1,3-dicarboxylato-κ 4 N:O:O':O')(1-methylpyrroldin-2-one-κ1O)dicopper(II)] – 1-methylpyrroldin-2-one (1/3), C40H48Cu2N12O12
  8. The crystal structure of 18-crown-6-k6O6(2,4,5-trinitroimidazol-1-ido-k1O)potassium(I)
  9. Crystal structure of poly[tetraaqua-bis(μ2-5-bromoisophthalato-κ3O,O:O)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N)dicadmium(II)] dihydrate
  10. Crystal structure of (5R,6S,E)-5-acetoxy-2-methyl-6-((2aR,3R,5aS,5bS,11aR,12aS)-2a,5a,8,8-tetramethyl-9-oxotetradecahydro-1H,12H-cyclopenta[a]cyclopropa[e]phenanthren-3-yl)hept-2-enoic acid, C32H48O5
  11. The crystal structure of poly[diaqua-bis(μ2 -thiocyanato-κ2N:O)cobalt(II) monohydrate
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  13. Crystal structure of dichlorido-bis(1-[(2-ethyl-benzimidazole-1-yl)methyl]-1H–benzotriazole) cadmium(II), C32H32CdN10OCl2
  14. The crystal structure of N′-(tert-butyl)-N′-(3,5-dimethylbenzoyl)-3-methoxy-N,2-dimethylbenzohydrazide, C23H30N2O3
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  18. The crystal structure of poly[hexaqua-tetrakis(μ4-pyridine-2,4-dicarboxylate-κ5N: O: O′: O″: O‴)-bi(μ2-pyridine-2,4-dicarboxylate-κ3N: O: O′)-digadolinium(III)tricopper (II)], [Gd2Cu3(C7H3NO4)6(H2O)6] n
  19. Crystal structure of poly[bis(4-(4-(pyridin-4-yl)phenyl)pyridin-1-ium-κ1N)-(μ4-benzene-1,2,4,5-tetracarboxylato-κ5O:O′: O″:O‴:O⁗)-(μ2-2,5-dicarboxyterephthalato-κ2O:O′)dizinc(II)], C52H32N4O16Zn2
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  27. Crystal and molecular structure of 5-bromopyridine-2,3-diamine
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  29. Crystal structure of thiocyanate-κ1N-bis(μ1-2,6-diformyl-4-methylphenol oxime-κ2N,O)-manganese(III) acetonitrile solvate, C21H21MnN6O6S
  30. The crystal structure of pyrrolidin-1-yl pivalate, C9H13NO4
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  53. The crystal structure of 6-amino-pyridinium-2-carboxylate, C6H6N2O2
  54. The crystal structure of catena-poly[aqua-nitrato-κ3O,O:O′′-(1,10-phenanthroline-κ2N,N)sodium(I)], C24H18N6O7Na2
  55. Retractions
  56. Retraction of: Crystal structure of bis[diaquaisonicotinatosamarium(III)]-µ-isonicotinato-[diisonicotinatocopper(II)], CuSm2(C6H4NO2)8(H2O)4
  57. Retraction of: Crystal structure of aqua(2,2-bipyridine-k 2 N:N′)(nitrato)-(4-aminobenzoato)cadmium(II) nitrate, [Cd(H2O)(NO3)(C10H8N2)(C7H7NO2)][NO3]
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