Synthesis and photophysical properties of novel multisubstituted benzene and naphthalene derivatives with high 2D-π-conjugation

• Novel multisubstituted benzene and naphthalene derivatives were synthesized.
• We analyze the influence of 2D-π-conjugation on their physical properties.
• Emitting properties were investigated.
• Electrochemical bad gap was compared to optical and calculated.
• Current–voltage characteristics for some derivatives were carried out.

A new small molecule, with D-A-D framework was prepared in good yield by using a [2+1+2+1] cycloaddition followed by the [4+2] Diels–Alders reaction. Additionally, tetra-substituted naphthalene derivatives were also prepared from in situ generated benzyne (using 2-trimethylsilylphenyl triflate and cesium fluoride). All of this compounds exhibit strong 2D-π-conjugation. The influence of this type of interactions on photophysical properties with the aid of DFT calculations was examined. The preliminary tests of application possibility of synthesized compounds in devices for optoelectronics were carried out as well.

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