1:1 and 2:1 cocrystallizations of alkoxy-substituted naphthalene derivatives with octafluoronaphthalene through arene–perfluoroarene interactions

•Alkoxy substituted naphthalenes were cocrystallized with octafluoronaphthalene.•Arene–perfluoroarene interaction is observed in the cocrystals.•The 2:1 cocrystal is rare example and each π-plane was highly overlapped.•Alkoxy groups at 2,7-position in naphthalene are effective for the cocrystallization.•Propoxy group is optimal to have possible CH⋯F interactions to give cocrystals.

Naphthalene derivatives with laterally orientated short side chains readily form cocrystals with octafluoronaphthalene in which the position and the length of the lateral chain can control the 1:1 and 2:1 cocrystallization stoichiometries and overlapped areas of the π-planes, showing that the systematic substitution patterns in the chains of molecules can be exploited to rationally designed cocrystals.

Graphical abstractNaphthalene derivatives with laterally orientated short side chains readily form unique 1:1 and 1:2 cocrystals with octafluoronaphthalene through arene–perfluoroarene interactions.Figure optionsDownload full-size imageDownload as PowerPoint slide