4,4′-Bis(2,2-diphenyl­vin­yl)-1,1′-biphen­yl

Liu, H.-N.; Zhang, G.; Hu, L.; Su, P.-F.; Li, Y.-F.

doi:10.1107/S1600536810052840

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o220

https://doi.org/10.1107/S1600536810052840

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4,4′-Bis(2,2-diphenylvinyl)-1,1′-biphenyl

Hong-Ni Liu,^a ^* Gao Zhang,^a Lan Hu,^a Peng-Fei Su ^a and Yun-Feng Li ^b

^aXi'an Modern Chemistry Research Institute, Xi'an 710065, People's Republic of China, and ^bXi'an Caijing Opto-Electrical Science & Technology Co. Ltd, Xi'an 710065, People's Republic of China
^*Correspondence e-mail: winny_521@163.com

(Received 6 December 2010; accepted 16 December 2010; online 24 December 2010)

The title molecule, C₄₀H₃₀, lies on an inversion center. The two unique phenyl rings form dihedral angles of 51.98 (8) and 67.58 (8)° with the essentially planar biphenyl unit [maximum deviation = 0.0360 (14) Å].

Related literature

For applications of the title compound, see: Park et al. (2005 ); Kim et al. (2009 ). For the preparation of the title compound, see: Zheng et al. (2004 ).

Experimental

Crystal data

C₄₀H₃₀
M_r = 510.7
Monoclinic, P 2₁ /c
a = 9.277 (2) Å
b = 14.625 (3) Å
c = 10.460 (2) Å
β = 92.669 (4)°
V = 1417.6 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.39 × 0.25 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
6984 measured reflections
2508 independent reflections
1479 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.110
S = 0.94
2508 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810052840/lh5185sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810052840/lh5185Isup2.hkl

checkCIF report

Comment top

Distyrylarylene (DSA) derivatives have been widely investigated because of there high thermal stability and good film forming ability. The title compound has been used to fabricate white organic light-emitting diodes (WOLEDs)(Kim et al., 2009; Park et al., 2005). The synthesis and luminescent properties of DPVBi have already been described (Zheng, et al. 2004). The molecular structure of the title compound is shown in Fig.1. The molecule lies on an inversion center. The two unique phenyl rings form dihedral angles of 51.98 (8) [for C9-C14] and 67.58 (8)° [for C15-C20] with the essentially planar biphenyl unit [maximum deviation = 0.0360 (14)Å]

Related literature top

For applications of the title compound, see: Park et al. (2005); Kim et al. (2009). For the preparation of the title compound, see: Zheng et al. (2004).

Experimental top

The synthesis of the crude product was carried out according to reported methods (Zheng, et al. 2004). Suitable crystals were obtained by evaporation of a tetrahydrofuran/methanol (1:9, v/v) solution of the title compound at room temperature. Spectroscopic analysis: IR(KBr, cm^-1): 3020,1597,1494,1441,762,697,815; ¹H NMR (CDCl₃, δ, p.p.m.): 7.3 (s, 20H), 6.9—7.2 (m, 10 H).

Structure description top

For applications of the title compound, see: Park et al. (2005); Kim et al. (2009). For the preparation of the title compound, see: Zheng et al. (2004).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms (symmetry code (A): 1-x, 2-y, -z).

4,4'-Bis(2,2-diphenylvinyl)-1,1'-biphenyl top

Crystal data top

C₄₀H₃₀	F(000) = 540
M_r = 510.7	D_x = 1.196 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 477 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.277 (2) Å	Cell parameters from 1536 reflections
b = 14.625 (3) Å	θ = 2.4–25.1°
c = 10.460 (2) Å	µ = 0.07 mm⁻¹
β = 92.669 (4)°	T = 296 K
V = 1417.6 (5) Å³	Block, yellow
Z = 2	0.39 × 0.25 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	1479 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 25.1°, θ_min = 2.4°
φ and ω scans	h = −11→10
6984 measured reflections	k = −17→17
2508 independent reflections	l = −12→10

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0637P)²] where P = (F_o² + 2F_c²)/3
2508 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₄₀H₃₀	V = 1417.6 (5) Å³
M_r = 510.7	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.277 (2) Å	µ = 0.07 mm⁻¹
b = 14.625 (3) Å	T = 296 K
c = 10.460 (2) Å	0.39 × 0.25 × 0.18 mm
β = 92.669 (4)°

Data collection top

Bruker SMART CCD diffractometer	1479 reflections with I > 2σ(I)
6984 measured reflections	R_int = 0.030
2508 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 0.94	Δρ_max = 0.12 e Å⁻³
2508 reflections	Δρ_min = −0.18 e Å⁻³
181 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.69791 (18)	0.84611 (10)	0.10768 (16)	0.0652 (5)
H1	0.6951	0.7855	0.1343	0.078*
C2	0.57204 (17)	0.88788 (10)	0.06689 (14)	0.0625 (4)
H2	0.4864	0.8549	0.0677	0.075*
C3	0.56784 (15)	0.97810 (9)	0.02422 (13)	0.0488 (4)
C4	0.69840 (17)	1.02440 (10)	0.03150 (16)	0.0633 (5)
H4	0.7009	1.0854	0.0066	0.076*
C5	0.82414 (17)	0.98268 (10)	0.07443 (16)	0.0642 (5)
H5	0.9088	1.0168	0.0795	0.077*
C6	0.82915 (16)	0.89105 (10)	0.11058 (13)	0.0539 (4)
C7	0.96931 (16)	0.85159 (11)	0.15032 (14)	0.0609 (4)
H7	1.0411	0.8943	0.1703	0.073*
C8	1.01194 (17)	0.76349 (10)	0.16283 (14)	0.0570 (4)
C9	1.16235 (17)	0.74195 (11)	0.20673 (15)	0.0599 (4)
C10	1.2386 (2)	0.79640 (12)	0.29442 (18)	0.0746 (5)
H10	1.1933	0.8464	0.3300	0.090*
C11	1.3807 (2)	0.77781 (13)	0.33001 (19)	0.0849 (6)
H11	1.4301	0.8155	0.3887	0.102*
C12	1.4498 (2)	0.70404 (14)	0.27931 (19)	0.0835 (6)
H12	1.5463	0.6923	0.3014	0.100*
C13	1.3742 (2)	0.64829 (16)	0.19597 (19)	0.0928 (6)
H13	1.4194	0.5974	0.1625	0.111*
C14	1.2324 (2)	0.66610 (13)	0.16054 (17)	0.0809 (5)
H14	1.1828	0.6265	0.1046	0.097*
C15	0.91607 (18)	0.68499 (10)	0.12923 (15)	0.0588 (4)
C16	0.86251 (18)	0.62995 (10)	0.22408 (15)	0.0630 (4)
H16	0.8899	0.6411	0.3093	0.076*
C17	0.7692 (2)	0.55891 (11)	0.19388 (18)	0.0730 (5)
H17	0.7328	0.5235	0.2588	0.088*
C18	0.7301 (2)	0.54030 (12)	0.0686 (2)	0.0828 (6)
H18	0.6666	0.4927	0.0485	0.099*
C19	0.7846 (2)	0.59197 (14)	−0.02639 (18)	0.0935 (6)
H19	0.7599	0.5786	−0.1115	0.112*
C20	0.8763 (2)	0.66401 (12)	0.00322 (17)	0.0815 (6)
H20	0.9120	0.6991	−0.0624	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0611 (11)	0.0537 (9)	0.0803 (12)	0.0013 (9)	−0.0031 (9)	0.0190 (8)
C2	0.0585 (11)	0.0566 (10)	0.0719 (11)	−0.0035 (8)	−0.0022 (8)	0.0120 (8)
C3	0.0532 (9)	0.0464 (8)	0.0472 (8)	0.0022 (7)	0.0066 (7)	−0.0038 (6)
C4	0.0540 (11)	0.0446 (8)	0.0918 (12)	0.0042 (8)	0.0095 (9)	0.0033 (8)
C5	0.0487 (10)	0.0507 (9)	0.0937 (12)	0.0002 (8)	0.0088 (9)	−0.0001 (8)
C6	0.0510 (10)	0.0550 (9)	0.0558 (9)	0.0048 (8)	0.0044 (7)	0.0019 (7)
C7	0.0555 (11)	0.0601 (10)	0.0673 (10)	0.0027 (8)	0.0046 (8)	0.0031 (8)
C8	0.0604 (10)	0.0573 (10)	0.0536 (10)	0.0061 (8)	0.0068 (7)	0.0043 (7)
C9	0.0627 (11)	0.0613 (10)	0.0560 (9)	0.0105 (8)	0.0052 (8)	0.0096 (8)
C10	0.0694 (13)	0.0656 (11)	0.0882 (13)	0.0097 (9)	−0.0017 (10)	0.0013 (9)
C11	0.0693 (13)	0.0806 (13)	0.1033 (15)	0.0018 (11)	−0.0101 (11)	0.0094 (11)
C12	0.0641 (12)	0.1014 (15)	0.0855 (15)	0.0166 (12)	0.0084 (11)	0.0284 (12)
C13	0.0890 (16)	0.1085 (16)	0.0810 (14)	0.0430 (13)	0.0047 (12)	0.0004 (12)
C14	0.0833 (14)	0.0875 (13)	0.0713 (12)	0.0301 (11)	−0.0033 (10)	−0.0057 (10)
C15	0.0696 (11)	0.0540 (9)	0.0531 (10)	0.0130 (8)	0.0038 (8)	0.0019 (7)
C16	0.0745 (11)	0.0573 (9)	0.0572 (10)	0.0107 (9)	0.0035 (8)	0.0040 (8)
C17	0.0866 (13)	0.0547 (10)	0.0784 (13)	0.0044 (9)	0.0127 (10)	0.0072 (9)
C18	0.0938 (15)	0.0632 (11)	0.0905 (15)	−0.0015 (10)	−0.0057 (12)	−0.0074 (11)
C19	0.1305 (18)	0.0808 (13)	0.0676 (12)	−0.0064 (13)	−0.0119 (12)	−0.0094 (11)
C20	0.1173 (17)	0.0712 (12)	0.0558 (11)	−0.0056 (11)	0.0041 (10)	0.0024 (9)

Geometric parameters (Å, º) top

C1—C2	1.368 (2)	C10—H10	0.9300
C1—C6	1.383 (2)	C11—C12	1.374 (2)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.3929 (19)	C12—C13	1.363 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.387 (2)	C13—C14	1.375 (3)
C3—C3ⁱ	1.481 (3)	C13—H13	0.9300
C4—C5	1.373 (2)	C14—H14	0.9300
C4—H4	0.9300	C15—C20	1.386 (2)
C5—C6	1.393 (2)	C15—C16	1.388 (2)
C5—H5	0.9300	C16—C17	1.379 (2)
C6—C7	1.465 (2)	C16—H16	0.9300
C7—C8	1.352 (2)	C17—C18	1.371 (2)
C7—H7	0.9300	C17—H17	0.9300
C8—C9	1.482 (2)	C18—C19	1.364 (3)
C8—C15	1.484 (2)	C18—H18	0.9300
C9—C10	1.384 (2)	C19—C20	1.380 (3)
C9—C14	1.384 (2)	C19—H19	0.9300
C10—C11	1.380 (3)	C20—H20	0.9300

C2—C1—C6	122.16 (14)	C12—C11—C10	120.49 (19)
C2—C1—H1	118.9	C12—C11—H11	119.8
C6—C1—H1	118.9	C10—C11—H11	119.8
C1—C2—C3	122.25 (15)	C13—C12—C11	118.78 (18)
C1—C2—H2	118.9	C13—C12—H12	120.6
C3—C2—H2	118.9	C11—C12—H12	120.6
C4—C3—C2	115.70 (14)	C12—C13—C14	121.05 (19)
C4—C3—C3ⁱ	122.27 (16)	C12—C13—H13	119.5
C2—C3—C3ⁱ	122.02 (17)	C14—C13—H13	119.5
C5—C4—C3	121.84 (14)	C13—C14—C9	121.11 (19)
C5—C4—H4	119.1	C13—C14—H14	119.4
C3—C4—H4	119.1	C9—C14—H14	119.4
C4—C5—C6	122.23 (15)	C20—C15—C16	117.58 (16)
C4—C5—H5	118.9	C20—C15—C8	121.76 (14)
C6—C5—H5	118.9	C16—C15—C8	120.66 (14)
C1—C6—C5	115.68 (14)	C17—C16—C15	120.99 (16)
C1—C6—C7	126.01 (14)	C17—C16—H16	119.5
C5—C6—C7	118.30 (14)	C15—C16—H16	119.5
C8—C7—C6	130.88 (15)	C18—C17—C16	120.27 (16)
C8—C7—H7	114.6	C18—C17—H17	119.9
C6—C7—H7	114.6	C16—C17—H17	119.9
C7—C8—C9	119.95 (15)	C19—C18—C17	119.70 (18)
C7—C8—C15	123.00 (14)	C19—C18—H18	120.1
C9—C8—C15	117.00 (13)	C17—C18—H18	120.1
C10—C9—C14	117.29 (16)	C18—C19—C20	120.32 (18)
C10—C9—C8	121.86 (14)	C18—C19—H19	119.8
C14—C9—C8	120.85 (16)	C20—C19—H19	119.8
C11—C10—C9	121.19 (17)	C19—C20—C15	121.09 (17)
C11—C10—H10	119.4	C19—C20—H20	119.5
C9—C10—H10	119.4	C15—C20—H20	119.5

C6—C1—C2—C3	0.7 (2)	C8—C9—C10—C11	−177.03 (15)
C1—C2—C3—C4	−3.0 (2)	C9—C10—C11—C12	−0.4 (3)
C1—C2—C3—C3ⁱ	177.73 (16)	C10—C11—C12—C13	−1.7 (3)
C2—C3—C4—C5	1.9 (2)	C11—C12—C13—C14	1.4 (3)
C3ⁱ—C3—C4—C5	−178.81 (15)	C12—C13—C14—C9	1.0 (3)
C3—C4—C5—C6	1.4 (2)	C10—C9—C14—C13	−3.0 (3)
C2—C1—C6—C5	2.6 (2)	C8—C9—C14—C13	176.71 (15)
C2—C1—C6—C7	−178.80 (14)	C7—C8—C15—C20	71.1 (2)
C4—C5—C6—C1	−3.7 (2)	C9—C8—C15—C20	−106.38 (18)
C4—C5—C6—C7	177.62 (14)	C7—C8—C15—C16	−108.71 (17)
C1—C6—C7—C8	17.8 (2)	C9—C8—C15—C16	73.86 (18)
C5—C6—C7—C8	−163.63 (15)	C20—C15—C16—C17	−2.1 (2)
C6—C7—C8—C9	−179.39 (14)	C8—C15—C16—C17	177.65 (14)
C6—C7—C8—C15	3.3 (2)	C15—C16—C17—C18	1.3 (2)
C7—C8—C9—C10	34.1 (2)	C16—C17—C18—C19	0.5 (3)
C15—C8—C9—C10	−148.38 (15)	C17—C18—C19—C20	−1.5 (3)
C7—C8—C9—C14	−145.60 (15)	C18—C19—C20—C15	0.6 (3)
C15—C8—C9—C14	31.9 (2)	C16—C15—C20—C19	1.2 (3)
C14—C9—C10—C11	2.7 (2)	C8—C15—C20—C19	−178.61 (16)

Symmetry code: (i) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₄₀H₃₀
M_r	510.7
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.277 (2), 14.625 (3), 10.460 (2)
β (°)	92.669 (4)
V (Å³)	1417.6 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.39 × 0.25 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6984, 2508, 1479
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.110, 0.94
No. of reflections	2508
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.18

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors are grateful for financial support from the Xi'an Modern Chemistry Institute (grant No. jcky28).

References

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