Systematic Structure–Property Investigations on a Series of Alternating Carbazole–Thiophene Oligomers

A series of alternating
carbazole–thiophene oligomers, namely
2,7-linked carbazole–thiophene oligomers 1, 3, 5, 7, and 9 and
3,6-linked ones 2, 4, 6, 8, and 10, in which the molecular length was
systematically elongated, were synthesized by Suzuki–Miyaura
coupling reactions. The effects of the conjugation connectivity between
the carbazole and thiophene moieties and the molecular length on the
electronic, photophysical, and electrochemical properties of 1–10 were comprehensively investigated.
In the present oligomer architectures, the connection with thiophene
at the 2,7-positions of carbazole ensures π-conjugation to a
high extent and high fluorescence quantum yields, while that at the
3,6-positions enhances the donor ability. The increase in the molecular
length of the 2,7-linked oligomers effectively extends π-conjugation.
The relationship between structural variations and photophysical properties
was examined by fluorescence lifetime measurements in detail. The
X-ray crystal structure of 6 was also disclosed.