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Polymorph crystal packing effects on charge transfer emission in the solid state

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Original languageEnglish
Pages (from-to)3525-3532
Number of pages8
JournalChemical Science
Issue number6
Publication statusPublished - 1 Jun 2015
Publication typeA1 Journal article-refereed


Condensation of 1,8-naphthalic anhydride with N,N-(dimethylamino)aniline produced the donor-acceptor compound DMIM, which crystallised from a chloroform-diethyl ether mixture to afford two different coloured crystal polymorphs. Crystals for one polymorph are small and green, whereas the other crystals are orange and needle-like. X-ray crystal structures for both polymorphs were determined. The donor N,N-dimethylaniline and acceptor naphthalimide groups are twisted with respect to each other; the degree of twist is marginally different for the two structures. The orange crystal polymorph crystallises in the monoclinic space group C2/c and contains two slightly different molecular conformers in the unit cell (calculated density is 1.410 g cm<sup>-3</sup>). The green crystal polymorph crystallises in the triclinic space group P1 and contains only one type of molecule in the unit cell (calculated density is 1.401 g cm<sup>-3</sup>). The crystal packing motifs for the two polymorphs are subtly different, explaining the small variance in the observed densities. Very weak room temperature emission was observed for DMIM in a CHCl<inf>3</inf> solution, but crystals deposited on a glass slide glowed when irradiated at 488 nm using a fluorescence microscope. Disparate solid-state emission spectra and lifetimes for the two polymorphic crystal forms are observed for the dyad. The emission is assigned to charge recombination fluorescence from a charge transfer state. This journal is

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Field of science, Statistics Finland