Luminescent benzo- and naphthoquinolines: Synthesis and investigation of photophysical properties

Visniakova, S.; Urbanavičiūtė, Indrė; Daukšaitė, Lauryna; Janulevicius, Matas; Lenkevičiūtė, Bronė; Sychugov, Ilya; Arlauskas, K.; Žilinskas, Antanas

doi:10.1016/j.jlumin.2015.06.052

Cited by 5 publications

(2 citation statements)

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“…[16] In contrast, several IPP-conjugated fluorophores within a well-known coumarin framework without solid-state fluorescence properties have been reported, [17][18][19][20] but fluorophores based on a quinoline and naphthyridine frameworks have been rarely reported. [21] In this report, we describe the preparation and photophysical properties of 1 and 2 in the solution and solid state. Moreover, the electronic states of 1 and 2 were evaluated in detail by experimental and computational methods.…”

Section: Introductionmentioning

confidence: 99%

“…In addition to organic synthesis, Yan and Ramström developed a fast and highly biorthogonal labeling method using stable IPP‐fragmented molecules [16] . In contrast, several IPP‐conjugated fluorophores within a well‐known coumarin framework without solid‐state fluorescence properties have been reported, [17–20] but fluorophores based on a quinoline and naphthyridine frameworks have been rarely reported [21] . In this report, we describe the preparation and photophysical properties of 1 and 2 in the solution and solid state.…”

Section: Introductionmentioning

confidence: 99%

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π‐Extended Push‐Pull‐Type Bicyclic Fluorophores Based on Quinoline and Naphthyridine Frameworks with an Iminophosphorane Fragment

2021

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Emissive quinoline and naphthyridine derivatives, bearing an iminophosphorane (IPP) fragment as an electrondonating group and two trifluoromethyl groups as electronwithdrawing groups, were prepared as electron push-pulltype bicyclic fluorophores: quinoline-IPP (1) and naphthyridine-IPP (2). Compared to those of the precursor bicyclic amines without the IPP moiety, the fluorescence quantum yields (Φ f ) of 1 and 2 were considerably higher, not only in low polarity solvents but also polar solvents. Moreover, the molar absorption coefficients (ɛ) were enhanced; thus, 1 and 2 are fluorophores with relatively high brightness (Φ f × ɛ). Using density functional theory calculations, the t indices were calculated, and these reveal that locally excited character is dominant in both molecules. Because of the sterically bulky IPP fragments, 1 and 2 emitted with moderate Φ f values, even in the solid state. Further, by exploiting the low crystallinity of 1 and 2, emissive amorphous thin films were prepared.

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