We describe the rational development of a design for pleochroic molecular solids, by using C-I center dot center dot center dot pi halogen bonds to pre-organise different chromophores in a cocrystal. Using the structure of a known naphthalene cocrystal as a blueprint, we demonstrate how a highly robust C-I center dot center dot center dot pi motif permits the systematic exchange of original cocrystal components with azobenzene and azulene, resulting in optically interesting dichroic or pleochroic materials.
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