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A series of 6,6′‐bis(O‐4‐arylethynylbenzoyl)‐α,α‐trehaloses (aryl groups; 1a: 1‐pyrenyl, 1b: 9‐anthryl, 1c: phenyl) were synthesized and fully characterized. Their photophysical properties were investigated by UV/Vis/fluorescence spectroscopy, and were rationalized by TDDFT calculations. Moreover, the emission maxima of 1a and 1b in THF/H2O considerably shifted to a longer wavelength region with increasing H2O fraction owing to the formation of excimers. The pyrenyl derivative 1a was efficiently taken into HeLa CD4+ human cervical cancer cells and emitted bright green fluorescence.

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