Bay Functionalized Perylenediimide with Pyridine Positional Isomers: NIR Absorption and Selective Colorimetric/Fluorescent Sensing of Fe3+ and Al3+ Ions

Abstract

Bay functionalized perylene diimide substituted with pyridine isomers, (2-pyridine (2HMP-PDI), 3-pyridine (3-HMP-PDI) and 4-pyridine (4-HMP-PDI)) have been synthesized and explored for selective coloro/fluorimetric sensing of heavy transition metal ions. HMP-PDIs showed strong NIR absorption (760-765 nm) in DMF. The absorption and fluorescence of HMP-PDIs have been tuned by make use of pyridine isomers. Reddish-orange color was observed for 2-HMP-PDI (λ = 437, 551, 765 nm) whereas 4-HMP-PDI exhibited light green (λ = 432, 522, 765 nm). 3-HMP-PDI showed orange-yellow (λ = 431, 524, 762 nm). The fluorescence spectra of 2-, 3- and 4-HMP-PDI showed λ at 585, 538, 546 nm, respectively. Interestingly, HMP-PDI dyes showed selective color change (intense pink color) and fluorescence quenching for Fe and Al metal ions in DMF. Absorbance spectra revealed complete disappearance of NIR absorption and intensification/appearance of new peak at lower wavelength. The concentration dependent studies suggest that 4-HMP-PDI can detect up to 36.52 ppb of Fe and 43.12 ppb of Al colorimetrically. The interference studies in presence of other metal ions confirmed the good selectivity for Fe and Al. The mechanistic studies indicate that Lewis acidic character of Fe and Al ions were responsible for selective color change and fluorescence quenching.

Perylene Diimide-Based Fluorescent and Colorimetric Sensors for Environmental Detection

“…The strong complexation between DSEA and Al 3+ leads to increase in fluorescence intensity via inhibiting the intramolecular PET process between DSEA and PDI core. Anthony [14] reported a series of PDIs substituted with pyridine isomers at the bay area, namely PDI-8 ( Figure 4c), and these PDIs demonstrated selective colorimetric and fluorescent sensing of Fe 3+ and Al 3+ ions from other interference cations in dimethylformamide (DMF). It was found, however, that it was not the above-mentioned metal coordination but the common Lewis acidic character of Fe 3+ and Al 3+ ions that was responsible for the observed sensing.…”

“…Combination of both fluorescence quenching and enhancement responses in signal processing leads to selective detection Hg 2+ (PDI-17) [24]. Similarly, improved selectivity can be achieved by incorporating both colorimetric and fluorescence responses, which have been employed for detecting various cations and anions as described above [8,9,14,49,58]. Some innovative molecular design of PDIs could make one single sensor to be capable of detecting simultaneously different cations and anions.…”

Fluorescent chemosensor based on organic nanofibril thin-films

“…速灵敏检测. 例如, 结果表明, 在分别暴露于TNT的饱 图 11 (a) ACTC分子结构与侧链效应引发的共平面构型 [46] ; (b) ACTC与爆炸物TNT、DNT和DMNB的能级结构及相应分子 结构; (c) 90 nm厚ACTC纳米线薄膜在暴露于TNT饱和蒸气(5 ppb)不同时间的荧光光谱(插图: DNT和TNT的荧光猝灭效率随 时间的变化, 以及ACTC纳米线薄膜的TEM图像) [46] ; (d) 暴露于2.7 ppm DMNB蒸气2 min之前和之后ACTC纳米线薄膜的荧光 光谱(插图: TEM图像) [48] (网络版彩图) [53] . 不仅…”

Synthesis and studies of bay‐substituted perylene diimide‐based D–A–D‐type SM acceptors for OSC and antimicrobial applications

“…Therefore, the crude product was subjected to imidisation without further purification. Imidisation of the anhydride with hexyl amine was carried out in high boiling solvents such as NMP and acetic acid [27]. Finally, Suzuki coupling was carried out between the brominated PDI and diverse thiophene boronic acid to synthesis the titled product.…”