Chalcogenolato-bridged ester functionalized rhenium(I) based rectangular metallacyclophanes l{(CO3)(3)Re(A-mu-ER)(2)Re(CO)(3)}2(mu-Pbin)(2)] (1, ER SC4H9, 2, ER SCH2C6H5, 3, ER SeC6H5) and hammock shaped metallacyclophanes [{(CO)(3)Re(A-ER)(2)Re(CO)(3)}(2)(mu-bpcpd)(2)] (4, ER SC4H9, 5, ER SCH2C6H5, 6, ER SC6H5, 7, ER SeC6H5) were obtained in one-pot reaction. The metallacyclophanes were synthesized by the reaction of ester functionalized ligands, phenyl-1,4-bisisonicotinate (pbin) and bis(4-(4pyridylcarboxyl)phenyl)dimethylmethane (bpcpd) with dialkyl/diaryl dichalcogenide and rhenium carbonyl. The tetranuclear compounds 1-7 were characterized using elemental analysis, IR, NMR and UV Vis spectroscopic techniques. Furthermore, compounds 2 and 6 were structurally characterized by single-crystal X-ray diffraction methods. Metallacyclophane 2 displayed a rectangular framework whereas the metallacyclophane 6 exhibited a hammock shaped structure. The molecular recognition capabilities of 2 and 6 were studied with few aromatic diamines. (C) 2018 Elsevier B.V. All rights reserved.