【摘 要】
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In this paper,two novel donor-acceptor (D-A) macrocyclic compounds 5 and 7 were successfully synthesized by post-functionalization of a planar dimer macrocycle (1) and a highly twisted trimer macrocycle (2),respectively,via controllable oxidation of metho
【机 构】
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Department of Chemistry and State Key Laboratory of Synthetic Chemistry,The University of Hong Kong,
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In this paper,two novel donor-acceptor (D-A) macrocyclic compounds 5 and 7 were successfully synthesized by post-functionalization of a planar dimer macrocycle (1) and a highly twisted trimer macrocycle (2),respectively,via controllable oxidation of methoxy groups and condensation between diketones and phenylenediamine in succession.Compared with unembellished 9,10-dimethoxyphenan-threne,the resultant dibenzo[a,c]phenazine motif is electron-deficient rather than electron-rich,yielding two D-A π-conjugated mac-rocycles with more contractive energy gaps.Density functional theory (DFT) calculations further support the unequivocal evidence of the D-A properties of macrocycles 5 and 7.The difference of their photophysical properties was investigated by the aid of ultravio-let-visible absorption and fluorescence spectrophotometers.Furthermore,the stacking patterns of 7 and its contrast π-conjugated macrocycle trimer (2) were compared via the analysis of X-ray single crystal,in which the electron-deficient dibenzo[a,c]phenazine unit provides extra interaction sites,resulting in orderly arrangement of 7 in the solid state.
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