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Synthesis of a 1,4‐Bis[2‐(5‐thiophen‐2‐yl)‐1‐benzothiophene]‐2,5‐dioctyloxybenzene Pentamer for Creatinine Detection
Author(s) -
Hidayah Azeman Nur,
Asif Ahmad Khushaini Muhammad,
Daik Rusli,
Ismail Ahmad Ghadafi,
Yeop Majlis Burhanuddin,
Mat Salleh Muhammad,
Aziz Tg Hasnan Tg Abdul,
Bakar Ahmad Ashrif A,
Md Zain Ahmad Rifqi,
Teh ChinHoong
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100374
Subject(s) - chemistry , pentamer , benzothiophene , thiophene , moiety , suzuki reaction , phosphole , hydrogen bond , phenylene , conjugated system , chlorobenzene , photochemistry , polymer chemistry , medicinal chemistry , organic chemistry , polymer , molecule , alkyl , aryl , biochemistry , catalysis
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 π‐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 υ(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 π‐π* transition between thiophene and bithiophene groups with 2,5‐bis(dioctyloxy)benzene moiety in the π‐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.