Synthesis, structural and spectral properties of diarylamino-functionalized pyrene derivatives via Buchwald-Hartwig amination reaction

Article abstract of DOI:10.1016/j.molstruc.2012.09.028

A new series of diarylamino-functionalized pyrene derivatives, namely, 1-(N,N-diarylamino)-substituted pyrenes (7), isomer of 1,6-bis- and 1,8-bis(N,N-diarylamino)-substituted pyrenes (8/9) and 1,3,6,8-tetrakis(N,N- diarylamino)-substituted pyrenes (10) have been synthesized. The structures of these synthesized compounds were determined on the basis of spectral data and elemental analysis. All compounds 7-10 have bright fluorescent emissions from sky-blue to green in solution condition (λ_max = 464-500 nm in CH₂Cl₂) and high emission efficiency (Φ_f = 0.84-0.96 in dichloromethane). All compounds have high thermal stability and good solubility in common organic solvents. The electronic properties of these compounds were determined by spectroscopic methods such as UV-vis absorption spectroscopy and fluorescence emission spectroscopy. Clear evidences were obtained that the longest wavelength bands of these compounds are bathochromically red-shifted as the number of the diarylamino-substituent increased.