The effect of –CF3 substitution position on the aggregation-induced emission, solvatofluorochromism and mechanofluorochromism properties of the conjugated 9-butyl-9H-carbazole phenylacrylonitrile derivatives

Suresh, Sumi K; Ramachandran, Lekshmi M; Krishnan, Aravind; Suneesh, Chettiyam Veettil

doi:10.1016/j.jphotochem.2023.114985

Cited by 5 publications

(3 citation statements)

References 52 publications

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“…For example, compound 3c displayed a quantum yield of 11% in a nonpolar solvent (hexanes), whereas it increased to 27% in acetonitrile, indicating a significant enhancement. This phenomenon can be attributed to the presence of a planarized intramolecular charge transfer (PLICT) state in compound 3c , as strongly supported by existing literature reports . The molecular architecture, induced by planarity, extends molecular conjugation, resulting in red-shifted emission of approximately 125 nm in polar ACN compared to hexane.…”

Section: Resultssupporting

confidence: 80%

Tailoring Emission Color Shifts in Mechanofluorochromic-Active AIE Systems of Carbazole-Based D−π–A Conjugates: Impact of π Spacer Unit Variants

Afrin,

Chinna Ayya Swamy

2024

J. Org. Chem.

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The expanding field of organic electronics has led to the emergence of donor−π–acceptor (D−π–A) systems as promising candidates for various optoelectronic applications. Recent advancements in the design of organic fluorophores allow precise modulation of their optical properties in the solution and solid states, broadening their utility. Here, we synthesize and characterize two series of D−π–A systems based on carbazole–cyanostilbene compounds (3a–c and 4a–c), which feature differences in π-spacer groups and substitution on the acceptor cyanostilbene units. These compounds exhibit intramolecular charge transfer (ICT) characteristics, with 3c possessing a phenyl spacer and −CF3 substitution displaying notable solvatochromism and polarity-enhanced emission (PEE). Additionally, both series show aggregation-induced emission (AIE), with emission color shifts controlled by spacer groups. These compounds demonstrate diverse emissive behaviors, including locally excited (LE), twisted intramolecular charge transfer (TICT), and π–π stacked aggregated states, contributing to the AIE phenomenon. Compounds with phenyl spacers (3a–c) exhibit higher solid-state quantum yields than those of thiophene (4a–c). Furthermore, the impact of spacer groups and acceptor substitutions on the solid-state emissive properties and mechanofluorochromism (MFC) are highlighted. Compounds with phenyl spacers and substitution (3a, 3c) show a blue-shifted MFC, while those with thiophene (4a, 4c) display a red-shifted MFC. These findings offer insights into the development of advanced materials with tunable emission properties and high thermal stability for optoelectronic applications.

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Section: Resultssupporting

confidence: 80%

Tailoring Emission Color Shifts in Mechanofluorochromic-Active AIE Systems of Carbazole-Based D−π–A Conjugates: Impact of π Spacer Unit Variants

Afrin,

Chinna Ayya Swamy

2024

J. Org. Chem.

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“…As reported, bipolar fluorophores with planar structures emit stronger fluorescence in high polarity solvents than in nonpolar solvents. 45–48 Accordingly, 7-AMCum molecules could generate more singlet excitons in highly polar PAA, PVA and PAN solid matrices. The dipole–dipole interactions between 7-AMCum and the polar hosts could reduce the energy level of low-lying singlet states; thus, the decreased Δ E ST facilitated SOCT-ISC.…”

Section: Resultsmentioning

confidence: 99%

Translating efficient fluorescence into persistent room-temperature phosphorescence by doping bipolar fluorophores into polar polymer matrix

Dong,

Liao,

et al. 2024

J. Mater. Chem. C

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“…Recently, in 2023, Suneesh et al created a series of 9-butyl-9H-carbazole derivatives 85 that exhibit strong solid-state emission with –CF 3 groups at various substituent positions of the phenyl group 21a–d , which have no, ortho , meta and para trifluoromethyl substitution, respectively (Fig. 15).…”

Section: Carbazole–cyanostilbene Derivatives With Different Terminal ...mentioning

confidence: 99%

Symphony of light: AIE and MFC in carbazole-based cyanostilbenes

Afrin,

Chinna Ayya Swamy

2024

J. Mater. Chem. C

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The effect of –CF3 substitution position on the aggregation-induced emission, solvatofluorochromism and mechanofluorochromism properties of the conjugated 9-butyl-9H-carbazole phenylacrylonitrile derivatives

Cited by 5 publications

References 52 publications

Tailoring Emission Color Shifts in Mechanofluorochromic-Active AIE Systems of Carbazole-Based D−π–A Conjugates: Impact of π Spacer Unit Variants

Tailoring Emission Color Shifts in Mechanofluorochromic-Active AIE Systems of Carbazole-Based D−π–A Conjugates: Impact of π Spacer Unit Variants

Translating efficient fluorescence into persistent room-temperature phosphorescence by doping bipolar fluorophores into polar polymer matrix

Symphony of light: AIE and MFC in carbazole-based cyanostilbenes

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