Communication
Pentacene-Based Polycyclic Aromatic Hydrocarbon Dyads with Cofacial Solid-State π-Stacking
Dan Lehnherr,
Adrian H. Murray,
Robert McDonald Dr.,
Michael J. Ferguson Dr.,
Rik R. Tykwinski Prof. Dr.,
Dan Lehnherr
Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada)
Search for more papers by this authorAdrian H. Murray
Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada)
Search for more papers by this authorRobert McDonald Dr.
X-Ray Crystallography Laboratory, Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada)
Search for more papers by this authorMichael J. Ferguson Dr.
X-Ray Crystallography Laboratory, Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada)
Search for more papers by this authorRik R. Tykwinski Prof. Dr.
Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada)
New address: Institut für Organische Chemie, Friedrich-Alexander-Universität, Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany)
Search for more papers by this authorDan Lehnherr,
Adrian H. Murray,
Robert McDonald Dr.,
Michael J. Ferguson Dr.,
Rik R. Tykwinski Prof. Dr.,
Dan Lehnherr
Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada)
Search for more papers by this authorAdrian H. Murray
Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada)
Search for more papers by this authorRobert McDonald Dr.
X-Ray Crystallography Laboratory, Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada)
Search for more papers by this authorMichael J. Ferguson Dr.
X-Ray Crystallography Laboratory, Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada)
Search for more papers by this authorRik R. Tykwinski Prof. Dr.
Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada)
New address: Institut für Organische Chemie, Friedrich-Alexander-Universität, Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany)
Search for more papers by this authorGraphical Abstract
Give me five! Pentacene-based polycyclic aromatic hydrocarbon (PAH) dyads are synthesized via an unsymmetrical pentacene building block. These molecules exhibit cofacial solid-state π-stacking as a result of the large aromatic chromophores. The choice of the PAH attached to the pentacene (see picture) influences the electronic properties as determined by UV/Vis absorption/emission spectroscopy and cyclic voltammetry.
Supporting Information
Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors.
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- 15aX-ray crystallographic data for 2 c: C45H40Si, Mr=608.86; crystal dimensions 0.46×0.40×0.24 mm; orthorombic space group Pna21 (no. 33); a=34.1011(13), b=13.6639(5), c=14.6209(6) Å; V=6812.7(5) Å3; Z=8; ρcalcd=1.187 g cm−3; μ=0.100 mm−1; λ=0.71073 Å; T=−100 °C; 2θmax=55.08°; total data collected=58 526; R1=0.0386 [13 955 observed reflections with [Fo2≥2σ(Fo2)]; wR2=0.1043 for 829 variables and 15 673 unique reflections with [Fo2≥−3σ(Fo2)]; residual electron density=0.453 and −0.254 e Å−3.
- 15bCCDC-736049 (2 b) CCDC-736050 (2 c), CCDC-736051 (2 d), CCDC-736052 (2 f) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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(no. 2); a=9.1190(10), b=12.8567(14), c=16.5030(18) Å; α=70.9187(13); β=83.3738(14), γ=82.2715(15)°; V=1806.6(3) Å3; Z=2; ρcalcd=1.211 g cm−3; μ=0.100 mm−1; λ=0.71073 Å; T=−100 °C; 2θmax=52.74°; total data collected=14 497; R1=0.0416 [5703 observed reflections with [Fo2≥2σ(Fo2)]; wR2=0.1147 for 451 variables and 7355 unique reflections with [Fo2≥−3σ(Fo2)]; residual electron density=0.279 and −0.244 e Å−3. See also ref. [15 b].
- 17X-ray crystallographic data for 2 f: C49H42Si, Mr=658.92; crystal dimensions 0.27×0.11×0.08 mm; triclinic space group P
(no. 2); a=8.5889(11), b=14.8703(19), c=15.312(2) Å; α=71.0863(16); β=81.8475(17), γ=78.8361(17)°; V=1808.4(4) Å3; Z=2; ρcalcd=1.210 g cm−3; μ=0.100 mm−1; λ=0.71073 Å; T=−100 °C; 2θmax=53.02°; total data collected=14 613; R1=0.0482 [5103 observed reflections with [Fo2≥2σ(Fo2)]; wR2=0.1324 for 451 variables and 7456 unique reflections with [Fo2≥−3σ(Fo2)]; residual electron density=0.390 and −0.367 e Å−3. See also ref. [15 b].
- 18X-ray crystallographic data for 2 b: C45H40Si, Mr=608.86; crystal dimensions 0.66×0.18×0.08 mm; triclinic space group P
(no. 2); a=7.6451(14), b=13.410(3), c=34.704(7) Å; α=88.638(2), β=84.211(2), γ=73.839(2)°; V=3399.9(11) Å3; Z=4; ρcalcd=1.189 g cm−3; μ=0.100 mm−1. λ=0.71073 Å; T=−100 °C; 2θmax=50.50°; total data collected=24 203; R1=0.0732 [6935 observed reflections with [Fo2≥2σ(Fo2)]; wR2=0.2164 for 863 variables, 72 restraints, and 12 272 unique reflections with [Fo2≥−3σ(Fo2)]; residual electron density=0.514 and −0.429 e Å−3. See also ref. [15 b]. The disordered isopropyl groups of molecule B were restrained to have the same geometry as that of one of the ordered isopropyl groups of molecule A by use of the SHELXL SAME instruction. Additionally, the SiC distances of the disordered triisopropylsilyl group were allowed to refine to a common value. Likewise, the CC distances of the secondary carbon atoms of the minor component were allowed to refine to a common value.
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