Alternated Stacks of Nonpolar Oligo(p‐phenyleneethynylene)‐BODIPY Systems

Abstract

Supramolecular chemistry: The self-assembly of an oligo(p-phenyleneethynylene)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (OPE-BODIPY) system into alternated 1D π stacks in solution exhibited liquid-crystalline properties at room temperature. This system represents a new approach towards a controlled dye organization exclusively driven by π-π interactions (see figure).

Influence of Ester versus Amide Linkers on the Supramolecular Polymerization Mechanisms of Planar BODIPY Dyes

“…[17,19] Previously described 4-iodophenyl-3,4,5-tris(dodecyloxy)benzoate [19d] and 3,4,5-tris(dodecyloxy)-N-(4-iodophenyl)benzamide [19c] were used as starting materials for the synthesis of compounds 5a and 5b through aS onogashira reaction in the presence of trime-thylsilylacetylene (TMS). [17,19] Previously described 4-iodophenyl-3,4,5-tris(dodecyloxy)benzoate [19d] and 3,4,5-tris(dodecyloxy)-N-(4-iodophenyl)benzamide [19c] were used as starting materials for the synthesis of compounds 5a and 5b through aS onogashira reaction in the presence of trime-thylsilylacetylene (TMS).…”

Fragmentation patterns of boron‐dipyrromethene (BODIPY) dyes by electrospray ionization high‐resolution tandem mass spectrometry

“…BODIPY dyes 1 , 9 and 10 were synthesized according to existing procedures . The methylated compounds 2 , 3 and 5 were produced as described previously . Methanol and formic acid were purchased from Sigma‐Aldrich (Steinheim, Germany).…”

Self-Assembly of Bodipy-Derived Extended π-Systems

“…3038 For instance, a Bodipy derivative 26 ( Figure 12a) functionalized with an oligo(p-phenyleneethynylene) (OPE) moiety and aliphatic side chains has been reported to form needle-like aggregates in solution and columnar rectangular LC phase in the bulk state. 67 Based on detailed photophysical, NMR and XRD studies, an alternate stack of Bodipy and OPE fragments have been suggested for solution state aggregates of 26, whereas molecules are reported to organize on top of each other in the LC phase.…”