Palladium (II)-catalyzed Sonogashira cross-coupling strategy was employed to synthesize a series of D-π-A-π-D type borondipyrromethene (BODIPY) derivatives equipped with fluorene and indenofluorene conjugations (Figure 1), which are supposed to exhibit enhanced two-photon absorption properties at NIR region. The conjugation between BODIPY and fluorene or indenofluorene moieties enables the efficient intramolecular electron transfer between the π arms and the BODIPY core. The HOMO and LUMO energy levels and energy band gap were studied by density functional theory (DFT) calculation (Figure 2). It was found that the electron density was distributed across the fluorene and indenofluorene unit in the HOMO contours of compound 1a-b, while the electron density was localized within the BODIPY core in the LUMO contours of compound 1a-b. In view of this, the dyes would display promising two-photon absorption properties.

Design and synthesis of BODIPY based two-photo absorbing fluorescent dyes

253rd National Meeting (2017)

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