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• BINOL-based chiral organic emitters have been synthesized. • The molecules with benzoxazole moieties display aggregation induced emission properties. • The molecules with quinazolinone moieties exhibit acidochromic properties. • Compound 5 has specific aggregation-induced circular dichroism enhancement property. The development of chiral organic fluorescent molecules has attracted broad attention for their various optical applications. In this work, four pairs of chiral fluorescent molecules based on binaphthanol structure have been designed and synthesized. These molecules show blue fluorescent emission in organic solvents with good fluorescent quantum yields and large Stokes shifts. The molecules with benzoxazole moiety display aggregation-induced emission effect in methanol/water solutions, while molecules with quinazolinone moiety show aggregation-caused quenching properties. Moreover, compounds with quinazolinone moiety exhibit acidochromic properties in aqueous solution with different pH values, and their emission intensity are significantly enhanced in strongly acidic conditions. The chiral molecules generally have good circular dichroism intensity. Their R- and S- enantiomers show mirror-imaged circular dichroism curves. Further studies reveal that compound with mono quinazolinone moiety has specific aggregation-induced circular dichroism enhancement properties. This work provides a new strategy for obtaining chiral BINOL-based fluorescent molecules with unique optical properties. BINOL-based chiral organic emitters with benzoxazole or quinazolinone moieties have been synthesized. These molecules exhibit aggregation induced emission, acidochromic and chiral optical properties. [Display omitted] [ABSTRACT FROM AUTHOR]

Organic fluorescent materials have been widely used in various fields including visualization of latent fingerprints and imaging of lysosomes. High-performance organic fluorescent molecules based on simple molecular structures are still limited and highly demanded for high-definition and high-contrast imaging of latent fingerprints and lysosomes. In this work, two organic fluorescent molecules (DANPAN and DANBEN) were developed based on dimethylamino naphthalenyl phenylethene structure. These two molecules have quite different fluorescent properties, and the position of cyano group significantly affects the optical properties of these dimethylamino naphthalenyl phenylethene derivatives. Compound DANPAN shows strong yellow emission in solid state, while compound DANBEN has strong fluorescent emission in organic solutions. In addition to these differences, both compounds have large Stokes shifts and positive solvatochromic properties. Further studies showed that these compounds could be used to display latent fingerprints on various substrate surfaces. The obtained fingerprint images have excellent contrast and high resolution. It is also found that these molecules could specifically stain lysosomes in living cell within short incubation time. This work provides a series of new high-performance organic fluorescent materials with diverse applications. Highly emissive dimethylamino naphthalenyl phenylethene derivatives have been synthesized, which show large Stokes shifts and positive solvatochromic properties. These compounds could be applied for visualization of latent fingerprints and specific localization of lysosomes in living cell imaging. [Display omitted] • Two dimethylamino naphthalenyl phenylethene derivatives are synthesized. • These molecules show large Stokes shifts and positive solvatochromic properties. • These compounds could be applied for visualization of latent fingerprints on various substrate surfaces. • These molecules could be used for specific localization of lysosomes in living cell imaging. [ABSTRACT FROM AUTHOR]