Racemic 9,10-diketo[7]helicene was successfully separated into enantiomers using a reversible and stereoselective reaction with 2,2'-diamino-1,1'-binaphthalene with moderate yields but with remarkable purity (>99% de). The enantiomerically pure diketone was used as a convenient starting material for the preparation of helicene-based push-pull molecules, which incorporated aza-aryl acceptors and diarylaminophenylene donor groups in a single step. A series of six push-pull systems, along with three reference molecules without donors, were prepared and studied using UV/vis and fluorescence measurements, circular dichroism, and DFT calculations.

Department of Inorganic Chemistry Faculty of Science Charles University Prague Hlavova 2030 128 40 Prague 2 Czech Republic

Department of Organic Chemistry University of Chemistry and Technology Technická 5 166 28 Prague 6 Czech Republic

Research Group of Advanced Materials and Organic Synthesis Institute of Chemical Process Fundamentals of the Czech Academy of Sciences v v i Rozvojová 135 165 00 Prague 6 Czech Republic

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