Designing chiral AIEgensw ithouta ggregation-induced emission (AIE)-active molecules externally tagged to the chiral scaffold remains al ong-standing challenge for the scientific community.T he inherenta ggregation-caused quenching phenomenon associated with the axially chiral (R)-[1,1'-binaphthalene]-2,2'-diol ((R)-BINOL)s caffold, together with its marginal Stokes shift, limits its applicationa sa chiral AIE-active material. Here, in our effort to designc hiral luminogens, we have developed ad esign strategy in which 2-substitutedf urans, when appropriately fused with the BINOLs caffold,w ill generates olid-state emissive materials with high thermala nd photostability as well as colour-tunable properties. The excellent biocompatibility,t ogetherw ith the high fluorescenceq uantum yield and large Stokes shift, of one of the luminogens stimulated us to investigate its cell-imaging potential. Thel uminogen was observedt ob e well internalised and uniformlyd ispersed within the cytoplasm of MDA-MB-231 cancer cells,s howingh ighf luorescence intensity.

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Synthesis of concave and vaulted 2H-pyran-fused BINOLs has been achieved. A regioselective, path-breaking concerted cascade route allows the placement of six-membered heteroaromatic rings at the sterically crowded 7,8 and 7′,8′ positions of BINOL. DFT studies with relative energetics that support the kinetically controlled reaction pathway are preferred, matching the experimental results. The new BINOLs exhibit smaller dihedral angle than BINOL on the diol part; this structural feature can be an assisting factor for better ligation with metals in the metal-catalyzed reactions. Corresponding C 2 symmetric [5] and [7]-oxa-helicenoids have an overlapping, sterically crowded geometry.

This work describes the design and synthesis of contorted dual emissive luminogen based on Tröger's base scaffold. The underlying principle of our design strategy was to use Tröger's base as the core scaffold and functionalize appropriately to avoid the detrimental π‐π stacking responsible for the emission quenching and induce RIR in the aggregated state and thereafter investigate their photophysical, electrochemical, and thermal properties. The unique white light emission of the fluorophores in the solid‐state together with excellent biocompatibility, photo, and thermal stabilities provided an opportunity for the application of one of the molecules for bacterial cell imaging. The luminogen was biocompatible and surprisingly possess an ability to selectively stain the dead bacterial cell debris, a unique property that can be exploited for the confirmation of cell lysis.

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