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A fundamental aspect\u00a0in this area is the development of novel strategies to construct supramolecular architectures with new (unusual) properties, in particular, strongly fluorescent H\u2010aggregates. Using 2\u2010(2\u2010carboalkoxy\u20103,4,5\u2010trichloro\u20106\u2010hydroxyphenyl)benzoxazoles (HBOs) as building blocks, H\u2010aggregates were successfully obtained in both aqueous binary mixtures and the crystalline state. These aggregates exhibit intense fluorescence despite the prohibition imposed by Kasha's rule. This violation seems to result from the deactivation mechanism\u00a0of the excited excitonic state in HBO H\u2010aggregates, which involves, along with internal conversion, a photochemical channel induced by excited\u2010state intramolecular proton transfer (ESIPT) rather than a radiative one. The consequence of ESIPT is monomeric fluorescence from the keto forms of HBOs. The fluorescence quantum yields of HBOs in the crystalline state are significantly higher than those in solution, ranging from 0.81 to 0.91. 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