Donor-Acceptor Complexes of Alkylcarbazole and Dicarbazolylalkane Donors with the Acceptors Tetracyanoethylene and Tetranitromethane

Journal of Physical Chemistry B

Volumn 104, Issue 10, 2000, Pages 2242-2250

  Haderski, Gary J ^a   Chen, Zhenhua ^a   Krafcik, Randolph B ^a   Masnovi, John ^a   Baker, Ronald J ^a   Towns, Robert L R ^a  

^a CLEVELAND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0004229569     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp9934174     Document Type: Article

References (76)

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37. Promotion of electrons from the same carbazole orbital(s) to different unoccupied orbitals of TCNE also is possible.
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39. 19.
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41. -1 for the TNM complexes.
42. 21.
43. + prevents an orientation in which the second carbazolyl group is able to interact electronically to stabilize the positive charge. The nitrile substituent of M3 also is separated from the carbazolyl group by an ethylene chain and would be expected to encounter similar geometric restrictions that would prevent an approach to the carbazolyl group favorable for complexation.
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47. 33 and averaging 1.435(7) Å for all of the dicarbazolylalkane derivatives.
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54. 37
55. Experimental observations and theoretical models suggest that aromatic rings prefer to associate in shifted stack structures, with stacking becoming increasingly favorable with increasing arene size: Jorgenson, W. L.; Severance, D. L. J. Am. Chem. Soc. 1990, 112, 4768.
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57. 38.
58. To distinguish the 1:1 complexes which form in solution from the crystalline complexes with different stoichiometries, the crystalline complexes formed from D2, D3, D4, MH, and M2 will be referred to as D2C, D3C, D4C, MHC, and M2C, respectively.
59. 42
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65. It also results in orientational disorder about the TCNE in these two complexes. Disorder of this sort for TCNE is reasonable, since the nearly square-planar geometry of the TCNE molecule allows packing to occur almost equally well in two crystallographically different but nearly equivalent orientations of the molecule.
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67. 51 Ellipsoidal objects give rise to values of k close to 0.72. The packing coefficients and the calculated densities for the dicarbazolylalkanes, along with those for crystals of carbazole, TCNE, are listed in Table 5. The k values for the dicarbazolylalkanes in this table fall in the range 0.67-0.72, which is typical for aromatic compounds. Among them, dicarbazolylmethane D1 has the highest packing coefficient. This higher k value for D1 might be attributed to the the short alkyl chain connecting the two carbazolyl rings of D1, so that the overall shape most closely approximates an ellipsoid (or, perhaps, a combination of two well-packed ellipsoids) than any other molecule within the group. The packing coefficients (k) for carbazolyl compound-TCNE EDA complexes and for crystals of their separate components are listed in Table 5. The packing coefficients for the EDA complexes with TCNE mostly are found to be very close to those of the corresponding uncomplexed donors.
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