Synthesis of a 1,4-Bis[2-(5-thiophen-2-yl)-1-benzothiophene]-2,5-dioctyloxybenzene Pentamer for Creatinine Detection

The synthesis of novel material 1,4-bis[2-(5-thiophen-2-yl)-1-benzothiophene]-2,5-dioctyloxybenzene pentamer (BOBzBT(2)) was carried out via Williamson etherification, bromination, and Suzuki coupling. Functionalization was carried out via the incorporation of dioctyloxy-substituents on phenylene moiety to improve its solubility. The elongation of the pi-conjugation backbone was carried out through the addition of benzo[b]thiophene rings of BOBzBT(2) to accelerate cation radicals ' formation. In FTIR, the disappearance of the stretching peak of upsilon(CBr) at 657 cm(-1) confirms the coupling of benzo[b]thiophene rings end-capped the BOBzBT(2) UV-visible shows the appearance of two broad bands at 343 nm and 422 nm, that related to pi-pi* transition between thiophene and bithiophene groups with 2,5-bis(dioctyloxy)benzene moiety in the pi-conjugated backbone, respectively. DSC shows that the BOBzBT(2) is a high purity compound. A gradual relaxation occurred between BOBzBT(2) with creatinine as observed in UV-visible analysis. It is expected that the BOBzBT(2) sensed creatinine via NH-S and NH-O hydrogen bonding interactions.

Automated summary

In this study, a novel material BOBzBT(2) with an extended pi-conjugation backbone was synthesized through functionalization and the addition of benzo[b]thiophene rings to improve solubility and promote cation radicals' formation. The disappearance of the stretching peak in FTIR confirmed the coupling of benzo[b]thiophene rings, and UV-visible analysis showed transitions related to the pi-pi* interactions between thiophene and bithiophene groups. The compound BOBzBT(2) exhibited high purity in DSC analysis, and showed interactions with creatinine through NH-S and NH-O hydrogen bonding.