Organic and Biomolecular Chemistry p. 6913 - 6920 (2017)
Update date:2022-08-04
Topics:
Kaiser, Reinhard P.
Mosinger, Ji?í
Císa?ová, Ivana
Kotora, Martin
Synthesis of selectively 4-substituted 9,9′-spirobifluorenes was accomplished by using catalytic [2 + 2 + 2]-cyclotrimerization of specifically substituted diynols with alkynes to the corresponding fluorenols. Further synthetic transformations provided the target molecules. The measurement of the photophysical properties of the prepared 4-substituted 9,9′-spirobifluorenes revealed that their emission maxima depended on the electronic properties of the substituents present in the para position: the presence of an electron accepting group strongly favored the maxima red shift toward the blue VIS region (CF3λmax = 361 nm vs. MeO λmax = 330 nm). Adding further substituents (aryl or arylethynyl moieties) on the phenyl ring in position 4 did not lead to a dramatic improvement in the emission maxima (CF3C6H4, λmax = 369 nm, CF3C6H4CC, λmax = 370 nm), but increased their quantum yields considerably. In addition, a series of 9,9′-spirobifluorenes possessing various extended π-systems (pyrene, anthracene, etc.) were synthesized. In general, the emission maxima pattern reflected that of the parent π-systems, but they were red shifted by 10-30 nm. Finally, also a 1-[4-(9,9′-spirobifluorene-4-yl)phenyl]-2-aryl-ortho-carborane was prepared. These data thus may provide guidelines for further design of 9,9′-spirobifluorenes with tailored properties.
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