Protein Detection and Quantitation by Tetraphenylethene-Based Fluorescent Probes with Aggregation-Induced Emission Characteristics

Abstract

Three functionalized derivatives of tetraphenylethylene (TPE), namely, 1,2-bis(4-methoxyphenyl)-1,2-diphenylethene (1), 1,2-bis(4-hydroxyphenyl)-1,2-diphenylethene (2), and 1,2-bis[4-(3-sulfonatopropoxyl)phenyl]-1,2-diphenylethene sodium salt (3), were synthesized and their fluorescence properties were investigated. All the TPE molecules are nonluminescent in the solution state but are induced to emit efficiently by aggregate formation. This novel process of aggregation-induced emission (AIE) is rationalized to be caused by the restriction of intramolecular rotations of the dye molecules in the aggregate state. The possibility of utilizing the AIE effect for protein detection and quantification is explored using bovine serum albumin (BSA) as a model protein, with salt 3 being found to perform as a stable, sensitive, and selective bioprobe.

Synthesis and fluorescent properties of conjugated copolymers containing maleimide and fluorene units at the main chain

“…47,48 2,7-dibromo-9,9 0 -dihexylfluorene (DBrDHF), 49,50 9,9 0 -dihexylfluorene-2,7-diboronic acid (DHFDBa), 51 2,3-bis(9,9-dihexylfluorene-3-yl)-N-cyclohexylmaleimide, 52,53 and each copolymers 35,54 were prepared by following the literature method. cyclohexyl), 1.76-1.92 (2H, m, cyclohexyl), 1.94-2.14 (2H, m, cyclohexyl), 3.90-4.10 (1H, m, @CHA).…”

“…35,54 The mixture was stirred at 60 C for 0.5 h under a nitrogen atmosphere, and then DICHMI (0.174 g, 0.803 mmol) in dry DMF (3 mL) was added. The reaction was maintained at 60 C for 48 h. The resultant mixture was poured into the dichloromethane (50 mL), and washed with 1N HCl and water.…”

New Chemo-/Biosensors with Silole and Tetraphenylethene Molecules Based on the Aggregation and Deaggregation Mechanism

“…They further designed the TPE derivative 14 with two anionic moieties for protein detection and quantitation [22]. Bovine serum albumin (BSA) at a concentration as low as 500 ng ml À1 was successfully detected with 14.…”

Synthesis and Functionality of Substituted Polyacetylenes

“…Retrostructural analysis of another AIE-active 1,1,2,2-tetraphenylethene (TPE) developed by us reveals that there is one common structural feature between TPE, and disubstituted poly(1-phenyl-1-octyne) 66 and poly(diphenylacetylene) 67: one or more aromatic peripheries are connected to an olefinic core [49][50][51][52][53]. In a dilute solution of TPE, intramolecular rotations of the aromatic rings against the olefinic core effectively and nonradiatively deactivate the excited states, thus making the molecules nonemissive (''off'').…”