Abstract
Transition metal catalyzed coupling reaction strategy has been utilized in the synthesis of two novel BN-perylenes starting from halogenated BN-naphthalene derivatives. The molecular structures and packing modes of BN-perylenes were confirmed by NMR spectroscopy and X-ray single-crystal diffraction experiments. Their photophysical properties were further investigated using UV-vis and fluorescence spectroscopy and DFT calculations. Interestingly, the isosteric BN-insertion in perylene system resulted in stronger π-π stacking interaction both in solid and solution phases. The synthesized BN-perylenes are proved to be highly stable and thus provide a new valuable platform for novel organic materials applications which is otherwise inaccessible to date.
Highlights
The advent of “the organic era” has gradually evolved and fostered to enrich the understanding and development at molecular levels in next-generation research areas of carbon materials, such as organic photo-catalysis, organic optoelectronics, organic photonics, organic spintronics as well as organic superconductors [1,2,3,4,5,6,7]
The syntheses of been observed for (BN)-substituted PAHs are still in a dormant phase with only sporadic reports and the study of BN-PAHs cannot be further sustained for lack of enumerating stable BN-aromatic building blocks, albeit this contradiction in reality is a shock of startling [24,25]
ABN dibromide 3b has been synthesized by our group, [32] whose ready availability provides a potential building block for BN-PAHs syntheses
Summary
The advent of “the organic era” has gradually evolved and fostered to enrich the understanding and development at molecular levels in next-generation research areas of carbon materials, such as organic photo-catalysis, organic optoelectronics, organic photonics, organic spintronics as well as organic superconductors [1,2,3,4,5,6,7]. At the required level of practical verisimilitude, structural tuning with heteroatom substitution of sp2-hybridized carbons becomes attractive with an aim to exquisitely control the electronic properties of carbon-rich conjugate systems [16,17,18,19,20]. In this respect, the isosteric substitution of C=C bond with B-N bond is used to influence the electronic density and energy levels of corresponding frontier molecular orbitals (e.g., HOMOs and LUMOs) and to modulate molecular properties such as band gap, optoelectronic and catalytic properties [21,22,23]. The paramount challenges come from the competence for orderly implementation of BN dipoles into the conjugate systems rather than some random choices, to precisely control both the orientation and quantity of the inserted BN dipoles
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