Synthesis and properties of novel extended BODIPYs with rigid skeletons

Kawamata, Yuki; Ito, Satoshi; Furuya, Masaru; Takahashi, Kyôko; Namai, Katsuya; Hashimoto, Saori; Roppongi, Makoto; Oba, Toru

doi:10.1016/j.tetlet.2019.01.046

Cited by 5 publications

(2 citation statements)

References 22 publications

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“…In the case of protonated dyes 5a–c , two fully reversible reduction processes separated by ∼300 mV can be observed in both CV and DPV at ∼ −1.2 and ∼ −1.5 V (Figure , Table , and Supporting Information Figures S102, S103). Despite the highly electron-deficient properties of these compounds, their irreversible oxidation can be observed around +1.3 V, which is anodically shifted compared to classical dipyrromethene systems. − On the other hand, zinc(II) complexes 8a–c are even more electron-deficient systems according to CV and DPV data. The first reduction potentials of these complexes are anodically shifted by ∼350 mV compared to protonated species 5a–c (−0.85 V for compounds 8a and 8c and −0.95 V for 8b ).…”

Section: Resultsmentioning

confidence: 99%

Development of a Class of Easily Scalable, Electron-Deficient, Core-Extended Benzo-Fused Azadipyrromethene Derivatives (“MB-DIPY”)

et al. 2019

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We have developed a new synthetic strategy for the preparation of a series of isoindolin-1-imines and isoindolin-1-ones from aromatic ketones and phthalonitrile. Self-condensation reactions of these isoindolin-1-imines led to the formation of a novel class of benzo-fused, highly electron-deficient core-extended azadipyrromethene chromophores ("MB-DIPY"). The influence of temperature, catalyst, and the template ions on the self-condensation reaction rate, yield, and stereoselectivity was examined in detail. New chromophores (sodium, zinc, and metal-free compounds) were characterized by NMR, UV−vis, fluorescence, high-resolution mass spectroscopies, and in many cases, Xray crystallography. Their redox properties were probed by electrochemical and spectroelectrochemical approaches that revealed the remarkable electron-accepting nature of the new systems. Stepwise one-and two-electron reduction of the new MB-DIPYs and their zinc complexes was investigated by spectroscopic and spectroelectrochemical methods. Both one-and two-electron reduced forms of all zinc complexes studied have strong absorption in the near-infrared region up to ∼1200 nm. Unusual spectroscopic and electrochemical properties of these dyes were correlated with their electronic structures and excitedstate natures predicted by density functional theory (DFT) and time-dependent DFT calculations. Despite some structural similarities with well-known aza-BODIPYs, the new MB-DIPYs differ remarkably from them in spectroscopic and redox properties.

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Section: Resultsmentioning

confidence: 99%

Development of a Class of Easily Scalable, Electron-Deficient, Core-Extended Benzo-Fused Azadipyrromethene Derivatives (“MB-DIPY”)

et al. 2019

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“…The starting chromenes 10 were prepared according to described procedures [ 41 , 42 , 43 ]. Compounds 13 – 15 were obtained according to the procedures analogous to those described in [ 44 , 45 , 46 ].…”

Section: Methodsmentioning

confidence: 99%