Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 2, Pages 1560-1574Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02404
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Funding
- DST [DST/TMD/SERI/D05(C)]
- INSA [SP/YSP/139/2017/2293]
- SERB [CRG/2018/000032]
- CSIR-New Delhi
- Indian Institute of Technology (IIT), Indore
- CSIR [01(2934)/18/EMR-II]
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This study focuses on the design and synthesis of phenanthroimidazole-based derivatives with different donor-acceptor structures, exhibiting aggregation-induced emission, solvatochromic, and mechanochromic behaviors. The research delves into the impact of variations in donor position, donor-acceptor strength, and introduction of spacer on the photophysical and electronic properties of the derivatives.
Organic materials possessing solid-state emission responsive to external stimuli have significance in a variety of material, biomedical, and optoelectronic applications. Organic molecules having different donor-acceptor architectures integrated with aggregation-induced emission (AIE) fluorophores have been utilized in development of mechanofluorochromic (MFC) materials. In this work, we have designed and synthesized phenanthroimidazole (PI) based derivatives TPE-PI-1, TPE-PI-2, TPE-PI-3, PTZ-PI-1, PTZ-PI-2, and PTZ-PI-3 where in donors tetraphenylethylene-TPE (D) and phenothiazine-PTZ (D') of contrasting donor abilities are attached to the N and C atom positions of PI. The position and mode of attachment of the donors have been changed, and an additional PTZ spacer has been introduced which has a direct consequence on their photophysical and electronic properties. The PI derivatives manifest AIE, solvatochromic, and mechanochromic behavior. The single crystal X-ray analysis of TPE-PI-1 and PTZ-PI-2 reveals bent structures for the PTZ unit and a twisted conformation for TPE moieties. The density functional theory calculations were used to obtain optimized ground-state structures of the PI derivatives. The work shows a comprehensive comparison of the photophysical, electronic, AIE, and MFC properties of the PI derivatives as an effect of variations in the position of donor, donor-acceptor strength, and change in molecular conformation on use of spacer.
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