Affiliation:
1. Institute of Organic Chemistry Polish Academy of Sciences Kasprzaka 44/52 01-224 Warsaw Poland
2. Institute of Physics Polish Academy of Sciences Aleja Lotników 32/46 02-668 Warsaw Poland
3. Department of Chemistry and Industrial Chemistry University of Pisa Via Moruzzi 13 56124 Pisa Italy
Abstract
AbstractChiral fluorescent macrocycles consisting of two to four units of dimethyl 2,5‐diaminoterephthalate can be readily synthesized in a one‐pot manner from inexpensive building blocks. Depending on the concentration, either a paracyclophane‐like dimer with closely stacked benzene rings or a triangular trimer is the main product of the reaction. The macrocycles exhibit fluorescence in solution as well as in the solid state with maxima that are red‐shifted with decreasing size of the macrocyclic ring and are observed at wavelengths from 590 (tetramer in solution) to 700 nm (dimer in the solid state). Chirality dictates the differential absorption and emission of circularly polarized light by these molecules. The ECD and CPL effects are particularly strong for the trimer, which is characterized by relatively large dissymmetry factors gabs=±2.8×10−3 at 531 nm and glum=±2.3×10−3 at 580 nm in n‐hexane, being at the same time highly luminescent (Φfl=13.7 %). Despite the small chromophore, the circularly polarized brightness BCPL of 2.3 dm3 mol−1 cm−1 is comparable to values reported for other classes of established CPL emitters in the visible region, such as expanded helicenes or larger π‐conjugated systems.
Subject
General Chemistry,Catalysis,Organic Chemistry
Cited by
1 articles.
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