2,5-Bis{2,2-bis­[4-(dimethyl­amino)­phen­yl]ethen­yl}-N,N′-diphenyl-N,N′-dipropyl­benzene-1,4-diamine

Schmitt, V.; Schollmeyer, D.; Detert, H.

doi:10.1107/S160053681100910X

Volume 67
Part 4
Page o876
April 2011

Received 8 March 2011
Accepted 9 March 2011
Online 12 March 2011

Key indicators
Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.004 Å
R = 0.074
wR = 0.232
Data-to-parameter ratio = 15.6
Details

2,5-Bis{2,2-bis[4-(dimethylamino)phenyl]ethenyl}-N,N'-diphenyl-N,N'-dipropylbenzene-1,4-diamine

Volker Schmitt,^a Dieter Schollmeyer ^a and Heiner Detert ^a ^*

^aUniversity Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
Correspondence e-mail: detert@uni-mainz.de

The title compound, C₆₀H₆₈N₆, was prepared by Horner olefination of a terephthaldialdehyde and a diarylmethyl phosphonate. There is one half-molecule, located on an inversion centre, in the asymmetric unit. The dihedral angle between the plane of the vinylene unit and the central ring is 36.79 (15)°, while those between the vinylene unit and the lateral phenyl rings are 53.04 (10) and 53.74 (9)°.

Related literature

For conjugated oligomers with basic sites as sensing materials for polarity and cations, see: Detert & Sugiono (2004, 2005); Wilson & Bunz (2005); Zucchero et al. (2009). For typical synthetic approaches to larger stilbenoid dyes, see: Drefahl & Plötner (1961); Stalmach et al. (1996). For crystal structures of phenylenevinylene oligomers, see: van Hutten et al. (1999); Detert et al. (2001). For optical properties of dyes which are highly sensitive towards environmental changes, see: Detert et al. (2001); Strehmel et al. (2003); Nemkovich et al. (2010). For the synthesis of the title compound, see: Schmitt (2005); Zheng et al. (2003).

Experimental

Crystal data

C₆₀H₆₈N₆
M_r = 873.20
Monoclinic, C 2/c
a = 20.485 (9) Å
b = 12.0782 (16) Å
c = 21.108 (9) Å
= 107.60 (2)°
V = 4978 (3) Å³
Z = 4
Cu K radiation
= 0.52 mm^-1
T = 193 K
0.50 × 0.30 × 0.20 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
4859 measured reflections
4720 independent reflections
3352 reflections with I > 2(I)
R_int = 0.064
3 standard reflections every 60 min intensity decay: 2%

Refinement

R[F² > 2(F²)] = 0.074
wR(F²) = 0.232
S = 1.09
4720 reflections
303 parameters
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.22 e Å^-3

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5488 ).

Acknowledgements

Financial support from the Deutsche Forschungsgemeinschaft is gratefully acknowledged.

References

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organic compounds