Aromatic π-stacking in solution as revealed through the aggregation of phenylacetylene macrocycles

Journal of the American Chemical Society

Volumn 118, Issue 5, 1996, Pages 1019-1027

  Shetty, Ashok S ^a   Zhang, Jinshan ^a,b   Moore, Jeffrey S ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b MOTOROLA INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND;

ARTICLE; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION;

EID: 0029935228     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9528893     Document Type: Article

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64. This finding is consistent with the study of a series of doubly substituted 1,8-diarylnaphthalenes in which it was found that electron withdrawing groups on the aromatic rings cause a higher barrier of rotation as a result of "less unfavorable" electrostatic interaction in the ground state. See: (a) Cozzi, F.; Ponzini, F.; Annuziata, R.; Cinquini, M.; Siegel, J. S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1019. (b) Cozzi, F.; Annuziata, R.; Cinquini, M.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 5330.
65. This finding is consistent with the study of a series of doubly substituted 1,8-diarylnaphthalenes in which it was found that electron withdrawing groups on the aromatic rings cause a higher barrier of rotation as a result of "less unfavorable" electrostatic interaction in the ground state. See: (a) Cozzi, F.; Ponzini, F.; Annuziata, R.; Cinquini, M.; Siegel, J. S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1019. (b) Cozzi, F.; Annuziata, R.; Cinquini, M.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 5330.
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67. Molecular modeling was done using QUANTA Version 4.0, Molecular Simulations, Inc.: Waltham, MA 02154.
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69. For a detailed analysis of the spatial distribution of aromatic-acetylene groups and a comparison to the random spatial distribution, see the supporting information.
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