Syntheses of Chlorophyllous Chlorin Derivatives with Aromatic Ring-Fused Imidazole Structural Unit

doi:10.6023/cjoc202006080

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1177-1186.DOI: 10.6023/cjoc202006080 Previous Articles Next Articles

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具有芳并咪唑结构单元的叶绿素类二氢卟吩衍生物的合成

张珠^a, 赵雨^b, 王欣悦^b, 李家柱^b, 王进军^a^,^b^,^*()

a 烟台大学文经学院食品与生物工程系山东烟台 264005
b 烟台大学化学化工学院烟台 264005

收稿日期:2020-06-30 修回日期:2020-10-19 发布日期:2020-11-04
通讯作者: 王进军
基金资助:
国家自然科学基金(21272048); 山东省自然科学基金(ZR2015BQ012)

Syntheses of Chlorophyllous Chlorin Derivatives with Aromatic Ring-Fused Imidazole Structural Unit

Zhu Zhang^a, Yu Zhao^b, Xinyue Wang^b, Jiazhu Li^b, Jinjun Wang^a^,^b^,^*()

a Department of Food & Biological Engineering, Wenjing College, Yantai University, Yantai, Shandong 264005
b College of Chemistry and Chemical Engineering, Yantai University, Yantai, Shandong 264005

Received:2020-06-30 Revised:2020-10-19 Published:2020-11-04
Contact: Jinjun Wang
About author:
* Corresponding author. E-mail: wjj1955@163.com
Supported by:
National Natural Science Foundations of China(21272048); Natural Science Foundation of Shandong Province(ZR2015BQ012)

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Abstract

Using pheophorbide-a methyl ester as starting material, the formyl group and α-diketone moiety were introduced into the water-soluble end of N²¹-N²³axis at different positions by the structural transformation on exocyclic ring. Furthermore, using the Phillps-Ladenburg-like reaction of active functional groups in chlorophyll chlorins with various aromatic o-diamines, the aromatic ring-fused imidazole structural units were created in linkage or fused manner, and a series of unreported chlorin derivatives that contain aryl-fused imidazol unit were finally synthesized. Besides, the relevant reaction mechanism was analyzed, and the absorption properties of these imidazolized products were discussed. The chemical structures of all newly synthesized compounds were characterized by elemental analysis, MS, UV-Vis, IR and ¹H NMR spectra.

Key words: Keywords chlorophyll, pheophorbide, chlorin, aromatic ring-fused imidazolization, synthesis

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Zhu Zhang, Yu Zhao, Xinyue Wang, Jiazhu Li, Jinjun Wang. Syntheses of Chlorophyllous Chlorin Derivatives with Aromatic Ring-Fused Imidazole Structural Unit[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1177-1186.

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Fig. & Tab. 7

Scheme 1. Synthesis of chlorins with benzmidazole unit 5~8 by condensation with o-arylenediamine (OPD) or 2,3-diaminonaphthalene (DAN) Reagents and conditions: (a) AcOH/reflux; (b) LiOH/O2/MeOH; (c) Pyr/TFA/OPD, 50 ℃; (d) Pyr/TFA/DAN, 50 ℃; (e) THF/TFA/OPD, r.t; (f) (1) pyr/MeONa/MeOH/O2, (2) NH2OH.

Scheme 2. Synthesis of chlorins with benzmidazole unit 9~14 by condensation of 2 with o-arylenediamine Reagents and conditions: (a) Pyr/TFA/DAN, 50 ℃; (b) THF/TFA/ODP, 50 ℃; (c) Pyr/TFA/ODP, 50 ℃; (d) Pyr/TFA/DABP, 50 ℃; (e) Pyr/TFA,50 ℃

Figure 1. Process of aryl-fused imidazolization at 12-position

Figure 2. Reaction of the carbonyl group of exocyclic ring with aromatic amine

Figure 3. Forming process of quinoxaline or benzimidazol-fused chlorins based on the reaction of 5 with OPD

Figure 4. Comparative electronic absorption spectra of 2a, 3, 8 and 14 (UV-Vis), and the normalized fluorescence spectra of compounds 3 (λex=412 nm), 8 (λex=429 nm) and 14 (λex=441 nm) (FL)

Figure 5. Substituent effect on the Qy maxima caused by non-covalent interaction at C-subring

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具有芳并咪唑结构单元的叶绿素类二氢卟吩衍生物的合成

Syntheses of Chlorophyllous Chlorin Derivatives with Aromatic Ring-Fused Imidazole Structural Unit

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