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Methanol soluble and stable guanosine octamers were successfully achieved via H-bond self-assembly. Through structural conformational design, we developed a new class of guanosine derivatives with modification on guanine (8-aryl) and ribose (2′,3′-isopropylidene). This unique design led to the formation of the first discrete G 8 -octamer with its structure characterized by single crystal X-ray diffraction, MS and NMR spectroscopy. The G 8 -octamer showed unique cation recognition properties, including the formation of a stable Rb + templated G-quadruplex. Based on this observation, further modification on the 8-aryl moiety was performed to incorporate a cross-layer H-bond or covalent linkage. Similar G-octamers were obtained in both cases with structures confirmed by single crystal X-ray diffraction. Furthermore, the covalently linked G-quadruplex exhibited excellent stability even in MeOH and DMSO, suggesting a promising future for this new H-bond self-assembly system in biological and material applications.