A(2)B- and A(3)-Type Boron(III)Subchlorins Derived from meso-Diethoxycarbonyltripyrrane: Synthesis and Photophysical Exploration
- Authors
- Soman, Rahul; Chandra, Brijesh; Bhat, Ishfaq A.; Kumar, B. Sathish; Hossain, Sk Saddam; Nandy, Sridatri; Jose, K. V. Jovan; Panda, Pradeepta K.
- Issue Date
- Aug-2021
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.86, no.15, pp.10280 - 10287
- Indexed
- SCIE
SCOPUS
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 86
- Number
- 15
- Start Page
- 10280
- End Page
- 10287
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/189712
- DOI
- 10.1021/acs.joc.1c01001
- ISSN
- 0022-3263
- Abstract
- The first direct fabrication of A(2)B- and A(3)-type B(III)-subchlorins from meso-ethoxycarbonyl-substituted tripyrrane has been realized by condensation with appropriate acid chlorides (benzoyl chloride, butyryl chloride, and ethyl chlorooxoacetate). The aliphatic acid chloride-based annulation reaction is new to subporphyrinoid chemistry. The phenyl (6a)- or n-propyl (6b)substituted derivatives could be oxidized to the corresponding B(III)-subporphyrins upon refluxing with DDQ, whereas the triethoxycarbonyl moiety (6c) was found to be resistant to oxidation and exhibits the most red-shifted absorption (587 nm) and emission (604 nm). The study indicates that absorption and emission behaviors of the B(III)subchlorin can be tuned by the introduction of electron-rich or electron-deficient substituents at the meso-position. B(III)subchlorins 6a and 6c generate singlet oxygen efficiently (44 and 40%, respectively) and, thus, may find application as potential photosensitizers in photodynamic therapy (PDT).
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