A facile synthesis of peri-naphthoindigo (PNI) was reported for the first time from simple precursor. Installation of a chromophore at the peri-position of naphthalene is very unique in terms of synthetic challenges and properties. PNI exists in monoenol form, undergoes halochromism in acidic medium, and displays a wide and strong absorption band (ε = 33390 Mcm) with maxima at 632 nm (chloroform). The dye undergoes oxidation and reduction at +0.30 and -0.58 V (vs Fc/Fc), respectively, in chloroform.

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Social benefit was observed at the molecular level via photoluminescence enhancement for all the participating components of a self-sorted co-aggregate of PNI and a naphthalimide derivative.