organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2,5-Bis[2-(4-methyl­phen­yl)ethyn­yl]benzyl methacrylate

aState Key Laboratory of Metastable Materials Science and Technology, Yanshan University, Qinhuangdao 066004, People's Republic of China
*Correspondence e-mail: hqzhang@ysu.edu.cn

(Received 1 July 2011; accepted 22 July 2011; online 30 July 2011)

In the title bis-tolane derivative, C29H24O2, the central benzene ring forms dihedral angles of 29.12 (9) and 26.46 (9)° with the other two benzene rings. The dihedral angle between two terminal benzene rings is 55.58 (8)°.

Related literature

For a related structure and the synthesis, see Zhang et al. (2010[Zhang, Z. L., Zhang, L. Y., Shen, Z. H., Chen, X. F., Xing, G. Z., Fan, X. H. & Zhou, Q. F. (2010). J. Polym. Sci. Part A Polym. Chem. 48, 4627-4639.]).

[Scheme 1]

Experimental

Crystal data
  • C29H24O2

  • Mr = 404.48

  • Monoclinic, P 21 /c

  • a = 13.479 (3) Å

  • b = 10.314 (2) Å

  • c = 18.390 (7) Å

  • β = 116.06 (2)°

  • V = 2296.7 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 293 K

  • 0.14 × 0.14 × 0.12 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.990, Tmax = 0.991

  • 21783 measured reflections

  • 5232 independent reflections

  • 3322 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.162

  • S = 1.05

  • 5232 reflections

  • 283 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.16 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku Corporation (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

High birefringence liquid crystals are useful not only in conventional display devices such as STNLCDs, but also in scattering-type PDLCDs as a reflective LCD, and in spatial light modulators.They are also of interest as componens of LCDs; for example, compensation films for improving the viewing angle, reflectors and polarizers. The bistolane derivatives is very important kind of high birefringence material. We have reported the similar synthesis of the compound in previous paper (Zhang et al. 2010). Herein we present the crystal structure of the title compound (see Fig. 1). All bond lengths and angles are in the normal ranges. The three benzene rings of the title compound are not coplanar, and the dihedral angles between the side-benzene rings and the central benzene ring are 29.12 (9)° and 26.46 (9)°, respectively. The dihedral angle between two terminal benzene rings is 55.58 (8)°. The crystal packing is stabilized by Van der Waals' force.

Related literature top

For a related structure and the synthesis, see Zhang et al. (2010).

Experimental top

The title compound was prepared according to the literature (Zhang et al., 2010). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a dichloromethane solution at room temperature.

Refinement top

H-atoms were placed in calculated positions and were included in the refinement in the riding model with C—H distances 0.93 Å for aromatic C—H and =CH2, 0.97 Å for —CH2— and 0.96 Å for —CH3. Uiso(H) = 1.5 Ueq(C) for methyl H atoms and 1.2 Ueq(C) for the rest H atoms.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The crystal structure of the title compound, with the atom numbering. Displacement ellipsoids of non-H atoms are drawn at the 30% probalility level.
2,5-Bis[2-(4-methylphenyl)ethynyl]benzyl 2-methylpropenoate top
Crystal data top
C29H24O2F(000) = 856
Mr = 404.48Dx = 1.170 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5232 reflections
a = 13.479 (3) Åθ = 3.0–27.5°
b = 10.314 (2) ŵ = 0.07 mm1
c = 18.390 (7) ÅT = 293 K
β = 116.06 (2)°Block, colourless
V = 2296.7 (11) Å30.14 × 0.14 × 0.12 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5232 independent reflections
Radiation source: fine-focus sealed tube3322 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1717
Tmin = 0.990, Tmax = 0.991k = 1313
21783 measured reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.090P)2 + 0.0263P]
where P = (Fo2 + 2Fc2)/3
5232 reflections(Δ/σ)max = 0.026
283 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C29H24O2V = 2296.7 (11) Å3
Mr = 404.48Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.479 (3) ŵ = 0.07 mm1
b = 10.314 (2) ÅT = 293 K
c = 18.390 (7) Å0.14 × 0.14 × 0.12 mm
β = 116.06 (2)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5232 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
3322 reflections with I > 2σ(I)
Tmin = 0.990, Tmax = 0.991Rint = 0.036
21783 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.162H-atom parameters constrained
S = 1.05Δρmax = 0.22 e Å3
5232 reflectionsΔρmin = 0.16 e Å3
283 parameters
Special details top

Experimental. (See detailed section in the paper)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
xyzUiso*/Ueq
O10.46919 (9)0.83960 (11)0.94444 (6)0.0577 (3)
O20.31533 (11)0.86679 (15)0.95953 (9)0.0855 (4)
C11.02239 (16)0.9345 (3)0.88082 (12)0.0898 (7)
H1A1.00370.95920.82600.135*
H1B1.08730.88110.90110.135*
H1C1.03641.01090.91370.135*
C20.92826 (13)0.8602 (2)0.88343 (9)0.0622 (5)
C30.85824 (15)0.9179 (2)0.90984 (10)0.0683 (5)
H30.87171.00290.92850.082*
C40.76866 (14)0.8535 (2)0.90948 (11)0.0657 (5)
H40.72280.89520.92780.079*
C50.74624 (12)0.72585 (18)0.88170 (9)0.0549 (4)
C60.81733 (13)0.66578 (19)0.85598 (9)0.0584 (4)
H60.80440.58060.83760.070*
C70.90735 (13)0.7320 (2)0.85748 (10)0.0620 (5)
H70.95490.69000.84080.074*
C80.65017 (13)0.66127 (19)0.87854 (10)0.0607 (4)
C90.56739 (13)0.61534 (18)0.87514 (9)0.0579 (4)
C100.46640 (12)0.56551 (16)0.87212 (9)0.0503 (4)
C110.42631 (11)0.61130 (15)0.92603 (8)0.0487 (4)
C120.32830 (12)0.56368 (16)0.92154 (9)0.0518 (4)
H120.30250.59330.95780.062*
C130.26695 (12)0.47142 (16)0.86327 (9)0.0524 (4)
C140.30682 (13)0.42763 (17)0.80977 (9)0.0559 (4)
H140.26630.36730.77030.067*
C150.40513 (13)0.47212 (17)0.81438 (9)0.0561 (4)
H150.43150.44010.77890.067*
C160.16510 (13)0.42429 (17)0.85986 (10)0.0588 (4)
C170.08020 (13)0.38608 (18)0.85793 (10)0.0609 (4)
C180.02216 (13)0.34409 (17)0.85662 (9)0.0545 (4)
C190.03831 (14)0.35079 (19)0.92580 (10)0.0648 (5)
H190.01880.37890.97410.078*
C200.13764 (15)0.3163 (2)0.92386 (10)0.0670 (5)
H200.14640.32120.97120.080*
C210.22507 (13)0.27457 (17)0.85347 (10)0.0587 (4)
C220.20792 (14)0.2662 (2)0.78517 (10)0.0677 (5)
H220.26510.23750.73710.081*
C230.10906 (14)0.2989 (2)0.78607 (10)0.0686 (5)
H230.09980.29080.73910.082*
C240.33470 (16)0.2402 (2)0.85113 (14)0.0862 (6)
H24A0.32420.17570.89150.129*
H24B0.38270.20660.79860.129*
H24C0.36730.31620.86170.129*
C250.48771 (13)0.71594 (16)0.98580 (9)0.0577 (4)
H25A0.46230.72001.02760.069*
H25B0.56610.69641.01140.069*
C260.37595 (13)0.90213 (17)0.93213 (9)0.0570 (4)
C270.35602 (14)1.01911 (17)0.87936 (9)0.0602 (4)
C280.42569 (17)1.0441 (2)0.84353 (11)0.0796 (6)
H28A0.40461.12430.81410.119*
H28B0.42020.97490.80710.119*
H28C0.50041.05050.88470.119*
C290.26432 (16)1.0942 (2)0.86929 (13)0.0811 (6)
H29A0.24611.16730.83640.097*
H29B0.22161.07090.89550.097*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0557 (7)0.0505 (7)0.0649 (7)0.0080 (5)0.0246 (5)0.0027 (5)
O20.0758 (9)0.0834 (10)0.1147 (11)0.0109 (7)0.0579 (8)0.0339 (8)
C10.0726 (13)0.118 (2)0.0835 (13)0.0401 (13)0.0388 (10)0.0140 (12)
C20.0500 (9)0.0826 (14)0.0505 (9)0.0163 (9)0.0190 (7)0.0017 (8)
C30.0696 (11)0.0693 (13)0.0667 (11)0.0188 (9)0.0305 (9)0.0104 (8)
C40.0583 (10)0.0750 (13)0.0695 (10)0.0031 (9)0.0334 (8)0.0063 (9)
C50.0429 (8)0.0647 (11)0.0548 (9)0.0044 (7)0.0193 (6)0.0062 (7)
C60.0491 (9)0.0597 (11)0.0597 (9)0.0011 (8)0.0178 (7)0.0045 (7)
C70.0459 (8)0.0798 (13)0.0599 (9)0.0026 (8)0.0231 (7)0.0046 (8)
C80.0467 (9)0.0706 (12)0.0620 (10)0.0033 (8)0.0211 (7)0.0084 (8)
C90.0472 (9)0.0640 (11)0.0593 (9)0.0022 (8)0.0206 (7)0.0073 (7)
C100.0401 (8)0.0523 (9)0.0531 (8)0.0007 (6)0.0154 (6)0.0107 (7)
C110.0421 (8)0.0456 (9)0.0494 (8)0.0001 (6)0.0119 (6)0.0084 (6)
C120.0463 (8)0.0525 (10)0.0553 (8)0.0007 (7)0.0212 (6)0.0069 (7)
C130.0424 (8)0.0476 (9)0.0612 (9)0.0024 (7)0.0171 (6)0.0080 (7)
C140.0509 (9)0.0536 (10)0.0554 (9)0.0065 (7)0.0161 (7)0.0009 (7)
C150.0523 (9)0.0583 (10)0.0573 (9)0.0020 (8)0.0237 (7)0.0023 (7)
C160.0479 (9)0.0551 (10)0.0690 (10)0.0053 (8)0.0216 (7)0.0021 (8)
C170.0507 (9)0.0574 (11)0.0724 (11)0.0068 (8)0.0249 (8)0.0017 (8)
C180.0501 (9)0.0485 (9)0.0641 (9)0.0054 (7)0.0245 (7)0.0030 (7)
C190.0566 (10)0.0726 (13)0.0562 (9)0.0077 (8)0.0166 (7)0.0021 (8)
C200.0693 (11)0.0791 (14)0.0604 (10)0.0067 (9)0.0358 (8)0.0004 (8)
C210.0548 (9)0.0561 (11)0.0700 (10)0.0057 (8)0.0320 (8)0.0037 (8)
C220.0567 (10)0.0817 (14)0.0618 (10)0.0236 (9)0.0233 (8)0.0106 (9)
C230.0653 (11)0.0865 (14)0.0605 (10)0.0212 (10)0.0335 (8)0.0097 (9)
C240.0667 (12)0.1030 (18)0.1036 (15)0.0148 (12)0.0509 (11)0.0018 (12)
C250.0532 (9)0.0528 (10)0.0553 (9)0.0048 (7)0.0131 (7)0.0041 (7)
C260.0530 (9)0.0551 (11)0.0582 (9)0.0084 (8)0.0201 (7)0.0009 (7)
C270.0602 (10)0.0513 (10)0.0579 (9)0.0139 (8)0.0157 (7)0.0005 (7)
C280.0817 (13)0.0797 (15)0.0774 (12)0.0135 (11)0.0350 (10)0.0150 (10)
C290.0765 (13)0.0589 (13)0.1095 (15)0.0069 (10)0.0422 (11)0.0221 (11)
Geometric parameters (Å, º) top
O1—C261.340 (2)C14—H140.9300
O1—C251.449 (2)C15—H150.9300
O2—C261.1900 (19)C16—C171.196 (2)
C1—C21.501 (2)C17—C181.436 (2)
C1—H1A0.9600C18—C191.383 (2)
C1—H1B0.9600C18—C231.392 (2)
C1—H1C0.9600C19—C201.371 (2)
C2—C31.372 (2)C19—H190.9300
C2—C71.392 (3)C20—C211.382 (2)
C3—C41.375 (2)C20—H200.9300
C3—H30.9300C21—C221.376 (2)
C4—C51.397 (3)C21—C241.502 (2)
C4—H40.9300C22—C231.368 (2)
C5—C61.387 (2)C22—H220.9300
C5—C81.434 (2)C23—H230.9300
C6—C71.382 (2)C24—H24A0.9600
C6—H60.9300C24—H24B0.9600
C7—H70.9300C24—H24C0.9600
C8—C91.188 (2)C25—H25A0.9700
C9—C101.433 (2)C25—H25B0.9700
C10—C151.402 (2)C26—C271.497 (2)
C10—C111.403 (2)C27—C281.388 (3)
C11—C121.377 (2)C27—C291.400 (3)
C11—C251.503 (2)C28—H28A0.9600
C12—C131.400 (2)C28—H28B0.9600
C12—H120.9300C28—H28C0.9600
C13—C141.388 (2)C29—H29A0.9300
C13—C161.431 (2)C29—H29B0.9300
C14—C151.369 (2)
C26—O1—C25116.40 (13)C16—C17—C18178.2 (2)
C2—C1—H1A109.5C19—C18—C23117.78 (15)
C2—C1—H1B109.5C19—C18—C17120.51 (15)
H1A—C1—H1B109.5C23—C18—C17121.69 (15)
C2—C1—H1C109.5C20—C19—C18120.65 (15)
H1A—C1—H1C109.5C20—C19—H19119.7
H1B—C1—H1C109.5C18—C19—H19119.7
C3—C2—C7117.78 (16)C19—C20—C21121.77 (15)
C3—C2—C1120.8 (2)C19—C20—H20119.1
C7—C2—C1121.40 (18)C21—C20—H20119.1
C2—C3—C4121.86 (19)C22—C21—C20117.29 (16)
C2—C3—H3119.1C22—C21—C24121.11 (16)
C4—C3—H3119.1C20—C21—C24121.60 (16)
C3—C4—C5120.34 (17)C23—C22—C21121.79 (15)
C3—C4—H4119.8C23—C22—H22119.1
C5—C4—H4119.8C21—C22—H22119.1
C6—C5—C4118.36 (16)C22—C23—C18120.68 (15)
C6—C5—C8121.69 (17)C22—C23—H23119.7
C4—C5—C8119.93 (16)C18—C23—H23119.7
C7—C6—C5120.30 (18)C21—C24—H24A109.5
C7—C6—H6119.9C21—C24—H24B109.5
C5—C6—H6119.9H24A—C24—H24B109.5
C6—C7—C2121.34 (17)C21—C24—H24C109.5
C6—C7—H7119.3H24A—C24—H24C109.5
C2—C7—H7119.3H24B—C24—H24C109.5
C9—C8—C5175.8 (2)O1—C25—C11109.61 (12)
C8—C9—C10177.4 (2)O1—C25—H25A109.7
C15—C10—C11118.99 (14)C11—C25—H25A109.7
C15—C10—C9120.60 (14)O1—C25—H25B109.7
C11—C10—C9120.40 (15)C11—C25—H25B109.7
C12—C11—C10119.64 (14)H25A—C25—H25B108.2
C12—C11—C25120.35 (14)O2—C26—O1123.25 (16)
C10—C11—C25119.95 (14)O2—C26—C27124.08 (17)
C11—C12—C13121.12 (14)O1—C26—C27112.66 (14)
C11—C12—H12119.4C28—C27—C29125.20 (18)
C13—C12—H12119.4C28—C27—C26119.44 (17)
C14—C13—C12118.78 (14)C29—C27—C26115.34 (16)
C14—C13—C16121.41 (15)C27—C28—H28A109.5
C12—C13—C16119.81 (15)C27—C28—H28B109.5
C15—C14—C13120.85 (15)H28A—C28—H28B109.5
C15—C14—H14119.6C27—C28—H28C109.5
C13—C14—H14119.6H28A—C28—H28C109.5
C14—C15—C10120.59 (15)H28B—C28—H28C109.5
C14—C15—H15119.7C27—C29—H29A120.0
C10—C15—H15119.7C27—C29—H29B120.0
C17—C16—C13179.05 (19)H29A—C29—H29B120.0
C7—C2—C3—C41.3 (3)C11—C10—C15—C141.0 (2)
C1—C2—C3—C4177.14 (16)C9—C10—C15—C14177.85 (14)
C2—C3—C4—C50.1 (3)C23—C18—C19—C201.3 (3)
C3—C4—C5—C61.0 (2)C17—C18—C19—C20177.03 (17)
C3—C4—C5—C8177.52 (15)C18—C19—C20—C210.3 (3)
C4—C5—C6—C70.5 (2)C19—C20—C21—C221.3 (3)
C8—C5—C6—C7178.01 (13)C19—C20—C21—C24178.41 (19)
C5—C6—C7—C20.9 (2)C20—C21—C22—C230.7 (3)
C3—C2—C7—C61.9 (2)C24—C21—C22—C23179.1 (2)
C1—C2—C7—C6176.61 (15)C21—C22—C23—C181.0 (3)
C15—C10—C11—C120.2 (2)C19—C18—C23—C222.0 (3)
C9—C10—C11—C12179.08 (14)C17—C18—C23—C22176.36 (18)
C15—C10—C11—C25177.08 (14)C26—O1—C25—C1183.10 (17)
C9—C10—C11—C251.8 (2)C12—C11—C25—O1102.30 (16)
C10—C11—C12—C130.9 (2)C10—C11—C25—O175.01 (18)
C25—C11—C12—C13176.44 (14)C25—O1—C26—O27.0 (2)
C11—C12—C13—C140.3 (2)C25—O1—C26—C27172.09 (13)
C11—C12—C13—C16179.67 (14)O2—C26—C27—C28173.18 (18)
C12—C13—C14—C151.0 (2)O1—C26—C27—C285.9 (2)
C16—C13—C14—C15179.08 (15)O2—C26—C27—C295.6 (3)
C13—C14—C15—C101.6 (2)O1—C26—C27—C29175.33 (15)

Experimental details

Crystal data
Chemical formulaC29H24O2
Mr404.48
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.479 (3), 10.314 (2), 18.390 (7)
β (°) 116.06 (2)
V3)2296.7 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.14 × 0.14 × 0.12
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.990, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
21783, 5232, 3322
Rint0.036
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.162, 1.05
No. of reflections5232
No. of parameters283
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.16

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

 

Acknowledgements

The authors acknowledge financial support by the Qinhuangdao Ministry of Science and Technology of China (201001 A020) and the Hebei Province Science Foundation of China (E2010001182).

References

First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku Corporation (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhang, Z. L., Zhang, L. Y., Shen, Z. H., Chen, X. F., Xing, G. Z., Fan, X. H. & Zhou, Q. F. (2010). J. Polym. Sci. Part A Polym. Chem. 48, 4627–4639.  Web of Science CrossRef CAS Google Scholar

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