The Synergistic Effect between Triphenylpyrrole Isomers as Donors, Linking Groups, and Acceptors on the Fluorescence Properties of D–π–A Compounds in the Solid State

Abstract

Eight donor-π-acceptor (D-π-A) compounds employing triphenylpyrrole isomers (TPP-1,2,5 and TPP-1,3,4) as donors, malononitrile (CN) and 1H-indene-1,3(2H)-dione (CO) as acceptors, pyridone (P) and benzopyran (B) as π-linking groups were synthesized. The compounds exhibited aggregation-induced emission and piezochromic properties. Compared with previously reported donors, triphenylpyrroles induced all the compounds to have more remarkable photophysical properties. The compounds containing TPP-1,2,5 and P moieties displayed stronger fluorescence intensities, shorter emission wavelengths, and more distinct piezochromic properties. However, the same phenomenon was observed in the TPP-1,3,4-containing system if B was as π-linker. Moreover, the CN acceptor endowed the compound to have a relatively strong fluorescent intensity, in which CO induced a relatively long emission wavelength. That is, the photophysical properties of D-π-A compounds can be controlled by adjusting the structure of donor, linker and acceptor.

Aggregation‐Induced Emission of Multiphenyl‐Substituted 1,3‐Butadiene Derivatives: Synthesis, Properties and Application

“…Mechanochromic luminogens with efficient solid‐state emission and large contrast are particularly desirable for practical applications . Limited examples of MPBs with AIE/AEE‐active mechanochromic luminogens have been reported.…”

“…Mechanochromic luminogens with efficient solid-state emission and large contrasta re particularly desirable for practical applications. [67][68][69][70][71][72] Limited examples of MPBs with AIE/AEEactive mechanochromic luminogens have been reported. The E/Z isomers of HPB-5 exhibited remarkable differences in the field of mechanochromic performance, as shown in Figure 5.…”

Real time bioimaging for mitochondria by taking the aggregation process of aggregation-induced emission near-infrared dyes with wash-free staining

“…21 In our recent work about AIE pyrole derivatives with varied D-A structures, we found that different acceptors and different substituted positions on the donors resulted in totally different photophysical properties such as emission wavelength and quantum yield. 22 Thus, we wanted to know how different donors or donor sizes with different photoluminescent (PL) properties affect their imaging efficiencies. However, a living organism is a very complex environment.…”

Aggregation‐Induced Emission‐Active 1,4‐Dihydropyridine‐Based Dual‐Phase Fluorescent Sensor with Multiple Functions

“…Furthermore, some 1,4‐dihydropyridine derivatives reportedly exhibit solid‐state fluorescence color changes upon external stimuli such as exposure to pressure, acidic vapor, organic vapor, and heat. Namely, they exhibit mechanochromic (MC), acidochromic, vapochromic, and thermochromic properties, respectively . However, 1,4‐dihydropyridine derivatives that exhibit stimulus‐responsive activities in both the solid and solution state are rarely reported.…”

“…Namely,t hey exhibit mechanochromic (MC), acidochromic, vapochromic, and thermochromic properties, respectively. [22][23][24][25][26][27] However,1 ,4dihydropyridine derivatives that exhibit stimulus-responsivea ctivitiesi nb oth the solid and solution state are rarely reported.…”