
%0 Journal Article
%A Hamilton, Darren G. 
%A Lynch, Daniel E. 
%A Byriel, Karl A. 
%A Kennard, Colin H. L. 
%T A Neutral Donor-Acceptor <font face = "symbol">p</font>-Stack: Solid-State Structures of 1 : 1 Pyromellitic Diimide-Dialkoxynaphthalene Cocrystals
%J Australian Journal of Chemistry
%D 1997/07/07
%V 50
%N 5
%P 439-446
%K 
%R https://doi.org/10.1071/C97033
%U https://www.publish.csiro.au/paper/C97033 
%X Pyromellitic diimide forms orange-coloured cocrystals of 1 : 1 stoichiometry with dialkoxynaphthalene derivatives. The solid-state structures of two examples are presented. The cocrystal formed with 2,6-dimethoxynaphthalene presents vertical stacks of alternating &#960;-rich and &#960;-deficient subunits with the long axes of the respective components approximately parallel. Investigation of the packing in the cocrystal also reveals a stabilizing array of hydrogen bonds between the components of adjacent stacks. Cocrystallization with 1,5-&#91;2-(2-hydroxyethoxy)ethoxy&#93;naphthalene, a derivative bearing hydroxy terminated ethyleneoxy chains, gives rise to an altered structural arrangement. Alternating donor- acceptor stacks once again dominate the structure but adopt a geometry where the long axes of the constituents are essentially perpendicular. Hydrogen-bonding interactions result in the formation of continuous non-covalently linked columns of donor and acceptor subunits by linking the terminal hydroxy functions of the naphthalene component to the imide protons. The structural preferences revealed by these solid-state analyses indicate that these complexes are useful prototypes of more complex neutral supramolecular assemblies. 
