Fluorophore-Labeling Tetraphenylethene Dyes Ranging from Visible to Near-Infrared Region: AIE Behavior, Performance in Solid State, and Bioimaging in Living Cells

Abstract

Functional molecules with aggregation-induced emission (AIE) have lately received the most attention due to their versatile functions in many fields. In this work, tetraphenylethene (TPE) as one of the most discussed AIE system was installed on different fluorophores including dansyl, naphthalimide, 4-nitro-1,2,3-benzoxadiazole (NBD), borondipyrromethene, and hemicyanine to afford a series of new fluorescent dyes, whose spectra covered the fluorescence region of the visible to near-infrared emission. Especially, these tetraphenylethene-containing compounds all exhibited AIE behavior. In solid state, they presented multiple colors including blue, orange, red, crimson, and NIR (near-infrared emission). It was worth mentioning that the dansyl-and NBD-coated TPEs exhibited obvious mechanoresponsive luminescence phenomena. Moreover, these AIE-based TPEs displayed a good bioimaging performance in living cells. This work will be helpful for designing functional AIE dyes with different fluorescence emission.

Stepwise Increase of NdIII‐Based Phosphorescence by AIE‐Active Sensitizer: Broadening the AIPE Family from Transition Metals to Discrete Near‐Infrared Lanthanide Complexes**

“…All these facts indicate that both L1 and L2 experience TICT by structure rigidification like previous reports. [19] As anticipated, the emission intensities of L1 and L2 were highly improved by increasing the poor solvent n-hexane contents in the mixed n-hexane/CHCl 3 solvents (Figure S8, Supporting Information). Beneficial from more TPE subunits in L1 than those in L2, the emission intensity in 90 % n-hexane for L1 was ca.…”

Aggregation-Induced Fluorogens in Bio-Detection, Tumor Imaging, and Therapy: A Review

“…On the other hand, the electron donor core probe units are conjugated with different acceptor molecules to afford a series of new AIEgens, whose spectra cover from visible to red. 18 Especially, the tetraphenylethene (TPE) AIEgens exhibits excellent AIE characteristics. 18 Introducing the anthraquinone acceptor into the TPE produced the emission towards the red region (4).…”

“…18 Especially, the tetraphenylethene (TPE) AIEgens exhibits excellent AIE characteristics. 18 Introducing the anthraquinone acceptor into the TPE produced the emission towards the red region (4). 19 The conjugation of TPE with the benzoselenodiazole dye brings the AIE emission by taking advantage of the polarization effect of selenium and with a strong D-π-A electronic property (5).…”

“…20 The HOMO and LUMO electron density of the TPE-hemicyanine molecules have chargetransfer characteristics with a low bandgap to shift the optical emission (6). 18 Occasionally, hijacking the ACQ to AIE have been realized for stable emission. 47 The red emissive fluorophores are converted from ACQ to AIE by conjugating with AIE molecules brings about AIE emission.…”

Recent Advances in Aggregation-Induced Emission Active Materials for Sensing of Biologically Important Molecules and Drug Delivery System

“…In 2019, Chen and coworkers demonstrated several fluorophores with tetraphenylethylene dye and dansyl, naphthalimide, 4-nitro-1,2,3-benzoxadiazole (NBD), borondipyrromethane (BODIPY), hemicyanine fluorophore in visible to near-infrared regions exhibiting AIE active effect. These fluorophores TPE-NIR, TPE-Blue, TPE-Crimson, TPE-Orange, and TPE-Red have been further explored in biological cell imaging, Figure 19 [ 98 ]. The AIE active TPE-containing fluorescent dyes have been then applied for the bioimaging in living cells, which covered the broad emission region.…”