Amphiphilic Fluorescence Resonance Energy‐Transfer Dyes: Synthesis, Fluorescence, and Aggregation Behavior in Water

Abstract

Amphiphilic pyrene/perylene bis‐chromophore dyes were synthesized from unsymmetrically substituted perylene bisimide dyes, which were obtained through three synthetic methods. The optical and aggregation behaviors of these functional dyes were studied by means of UV/Vis absorption and fluorescence spectroscopy, dynamic light scattering, and TEM. These dyes are highly fluorescent and cover the whole visible‐light region. A donor/acceptor dye displays intramolecular fluorescence resonance energy transfer (FRET), with a high efficiency of up to 96.4 % from pyrene to perylene bisimide chromophores, which leads to a high fluorescence color sensitivity to environmental polarity. Under a λ=365 nm UV lamp, the light‐emitting colors of the donor/acceptor dye change from green to yellow with increasing solvent polarity, which demonstrates application potential as a new class of FERT probes. The donor/acceptor dye in water was assembled into hollow vesicles with a narrow size distribution. The bilayer structure of the vesicular wall was directly observed by means of TEM. These vesicular aggregates in water are fluorescent at λ=650–850 nm within the near‐infrared region.

Modulating Energy Transfer and Light‐Emitting Colors by Chiral Dye Exchange and Achiral‐to‐Chiral Dye Conversion

“…Compared to the small Stokes shift (33 nm) of pure donor dye exo ‐ 2 , donor‐acceptor dye exo ‐ 3 displays extremely large Stokes shift up to 168 nm due to energy transfer. Large Stokes shift dyes remain always attractive for practical applications as fluorescence probes and sensors [17–23] . Exo ‐ 2 contains only pyrene fluorophore, and its fluorescence lifetime was measured to be 29.8 ns (Figure 7a).…”

“…Large Stokes shift dyes remain always attractive for practical applications as fluorescence probes and sensors. [17][18][19][20][21][22][23] Exo-2 contains only pyrene fluorophore, and its fluorescence lifetime was measured to be 29.8 ns (Figure 7a). Exo-3 contains both pyrene donor and dansyl acceptor, and its pyrene donor lifetime was measured to be 2.7 ns (Figure 7b).…”

New dual-mode orthogonal tunable fluorescence systems based on cucurbit[8]uril: White light, 3D printing, and anti-counterfeit applications

“…[11] The interest in PDI stems from its inherent desirable properties that include electron-accepting ability, enhanced thermal and optical properties, high extinction coefficients, and excellent quantum yields. [12][13][14][15][16][17][18][19] In water, the planar conjugated structure tends to promote π-π stacking and a lack of fluorescence.…”

“…The presence of the Q[n] aids the depolymerization process and allows for the formation of fluorescent supramolecular systems. [13][14][15][16][17][18][19][20][21][22][23][24] By varying other parameters such as pH, the emission can be controlled, for example, to produce white light. [25][26][27][28][29][30][31] The presence of other guests can also impact the behavior of the system.…”

New Dual-Mode Orthogonal Tunable Fluorescence Systems Based on Cucurbit[8]Uril: White Light, 3d Printing and Anti-Counterfeit Applications

“…[11] The interest in PDI stems from its inherent desirable properties that include electron-accepting ability, enhanced thermal and optical properties, high extinction coefficients, and excellent quantum yields. [12][13][14][15][16][17][18][19] In water, the planar conjugated structure tends to promote π-π stacking and a lack of fluorescence.…”