Benzosiloles with Crystallization‐Induced Emission Enhancement of Electrochemiluminescence: Synthesis, Electrochemistry, and Crystallography

Abstract

Crystallization‐induced emission enhancement (CIEE) was demonstrated for the first time for electrochemilunimescence (ECL) with two new benzosiloles. Compared with their solution, the films of the two benzosiloles gave CIEE of 24 and 16 times. The mechanism of the CIEE‐ECL was examined by spooling ECL spectroscopy, X‐ray crystal structure analysis, photoluminescence, and DFT calculations. This CIEE‐ECL system is a complement to the well‐established aggregation‐induced emission enhancement (AIEE) systems. Unique intermolecular interactions are noted in the crystalline chromophore. The first heterogeneous ECL system is established for organic compounds with highly hydrophobic properties.

Aggregation-Induced Emission in Electrochemiluminescence: Advances and Perspectives

“…An extension of the silole's work was described by the group of Pagenkopf [61] who extended the concept of crystallization-induced emission enhancement [62] to benzosilole systems displaying enhanced AIECL in the crystalline state rather than in the amorphous aggregates. The synthesized compounds (4T1 and 4T2; Fig.…”

“…AIECL represents a strategy capable not only of overcoming the limitations of ECL applications in aqueous, biological and environmental media but also to increase the sensing capabilities of existing ECL platforms. The introduction of new or imported concepts that enrich the AIECL toolbox, such as RIM, [49], HAIE-ECL [59], CIEE [61] or SS-AIECL [74], is important to feed the creativity that underlies the conception of more powerful materials capable of detecting the more challenging analytes in the most diverse conditions. Until now, just a handful of the abundant collection of known AIE luminophores have been explored in AIECL, and the expansion to more diverse systems provides AIECL with an important potential that still needs to be explored; in addition, pursuing the de novo design of luminogens specifically for AIECL also has a boundless potential.…”

Film Electrochemiluminescence Controlled by Interfacial Reactions Along with Aggregation‐, Matrix‐Coordination‐, and Crystallization‐Induced Emissions

“…Yang, Ding and Pagenkopf et al. sought to find CIECL for the first time with a π‐conjugated benzosilole complex (BSC) [50] . The structures of the studied BSC is displayed in Figure 6a.…”

“…The right inset displays a photo of the electrochemical cell used for the ECL experiments under 265 nm irradiation with an apparent yellow film on the glassy carbon electrode. Reprinted from ref [50]. with permission from Wiley-VCH.…”

Optimizing the Electrochemiluminescence of Readily Accessible Pyrido[1,2‐α]pyrimidines through “Green” Substituent Regulation

“…Nevertheless, the electrochemiluminophores are inarguably the most important part for ECL based techniques. Inorganic metal complexes, organic compounds and luminescent nanoparticles (or quantum dots) are three main classes of electrochemiluminophores, among which the organic compounds are anticipated to be prominent candidates for ECL because of their inherent capability for structural modifications and functionalization leading to fine‐tuning ECL emission band and efficiency [16–18] . Elangovan and co‐worker [19] synthesized a series of donor‐substituted phenylethynylanthronitriles and found that their ECL emissions are greatly dependent on chemical structures.…”