Functionalization of meso-positions of calix[4]pyrroles is the most viable strategy to design topologically new receptors with tunable guest binding properties. In recent years, meso-aryl calix[4]pyrroles have been extensively studied as effective receptors for anions, ion-pairs and transmembrane anion transporters where the electronic natures of meso-substituents play crucial roles.1 Meso-aryl calix[4]pyrroles usually adopted cone conformation during anion complexation and anion binding occurred in between the axially positioned meso-aryl groups. Moreover, existence of attractive or repulsive interactions between the π-systems of installed meso-aryl groups and anions are well established with variety of model systems. We have designed and synthesized a series of meso-bis-arylethynyl calix[4]pyrroles by directly anchoring ethynyl groups at the diametrical opposed meso-positions.2 Meso-substituted calix[4]pyrroles containing direct meso-ethynyl linker displayed high binding affinities and unique conformational features on halide anion binding. A general conformational bias for the equatorial alignments of the meso-(aryl)ethynyl groups were observed in the host-halide complexes which was attributed to the repulsive anion-alkyne interactions and released steric strain. Synthetic details, conformational features and comparative halide anion binding properties will be presented.