Issue 13, 2022

A phenothiazine-fused electroactive bilayer helicene: design, synthesis, ACQ-to-AIE transformation and photophysical properties

Abstract

π-Extended helicenes and their derivatives represent green polycyclic aromatic hydrocarbons. Here, we report the design and synthesis of a novel phenothiazine and perylene diimide (PDI)-fused [7]helicene, represented as SPS-PY-PT, to study the aggregation-induced emission (AIE) phenomenon along with its photophysical and electroactive properties. The conventional strategy for AIE uses a twisted molecule or core-connected twisted molecules. However, the present strategy has shown perylene itself as a twisted structure in SPS-PY-PT, which shows effective AIE properties. In contrast, uncyclized PY-PT-Un shows aggregation-caused quenching (ACQ) rather than the AIE phenomenon. Further, the photoconductive properties of SPS-PY-PT were examined by time-resolved microwave conductivity (TRMC). The transient photoconductivity shows a great increase on mixing with a poly-3-hexylthiophene (P3HT) polymer donor, indicating an efficient electron transfer from P3HT to SPS-PY-PT. Electrochemical analyses are conducted and correlated with theoretical calculations. The photophysical and electrochemical data suggest that SPS-PY-PT can be used as an electron acceptor for organic photovoltaics and additionally gives a direction towards AIE-based sensors.

Graphical abstract: A phenothiazine-fused electroactive bilayer helicene: design, synthesis, ACQ-to-AIE transformation and photophysical properties

Supplementary files

Article information

Article type
Paper
Submitted
23 Ker. 2021
Accepted
17 Cʼhwe. 2022
First published
17 Cʼhwe. 2022

J. Mater. Chem. C, 2022,10, 5173-5182

A phenothiazine-fused electroactive bilayer helicene: design, synthesis, ACQ-to-AIE transformation and photophysical properties

B. S. Shivaji, R. Boddula, A. Saeki and S. P. Singh, J. Mater. Chem. C, 2022, 10, 5173 DOI: 10.1039/D1TC06090B

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