Page 125 - 《精细化工》2021年第9期
P. 125

第 9 期                    马   卉,等:  聚卟啉的制备及其在光氧化催化反应中的应用                                 ·1839·


            的峰面积比为 73∶26。综上,证明了该类催化剂,                          有良好的催化活性及较高的底物普适性,对于 C—S
            尤其是优选的 PPOP-1 对于 C—N 的有氧氧化体系具                      的有氧氧化具有较大的研究潜力。

                                         表 1  PPOP-1 光催化氧化的底物、产物及转化率
                          Table 1    Substrates, products and conversion rates of photocatalytic oxidation by PPOP-1
                            底物                                 产物                     时间/h         转化率/%

                                                                                        12           99


                                                                                        12           99



                                                                                        24           99



                                                                                                     26

                                                                                        24

                                                                                                     73

                 注:反应条件与 1.3 节所述 PPOP-1 氧化二苄胺反应一致,即准确称量底物(0.1 mmol)和 PPOP-1(0.01 mmol)置于 10 mL 反
            应瓶里,加入 1 mL 乙腈(底物浓度为 0.1 mol/L),反应瓶敞口放置,室温下用白灯(28 W)照射并定时取样(灯与样品距离 10 cm)。

            3   结论                                             [8]   Journal of Inorganic Chemistry (无机化学学报), 2007, 23(1): 1-14.
                                                                   JIN X M (金晓敏), WU J (吴健). Progress in  porphyrins as a
                                                                   photosensitizing drug for photodynamic therapy[J]. Chinese Journal
                 本文制备了两种结构的卟啉单体——双溴双炔                              of Medicinal Chemistry (中国药物化学杂志), 2002, 12(1): 52-56.
                                                               [9]   HUANG D (黄丹), TIAN S (田澍).  The research development of
            卟啉和四溴卟啉,分别通过自聚和共聚制备了 4 种                               porphyrins and metalloporphyrins[J]. Journal of Jiangsu Polytechnic
                                                                   University (江苏石油化工学院学报), 2003, 15(3): 19-23.
            多孔有机聚卟啉。SEM 和氮气吸附-脱附曲线表明,                          [10] WANG  L  Y  (汪凌云), CAO D R (曹德榕). Research advances of
                                                                   porphyrin photosensitizers in photodynamic therapy[J]. Chinese Journal
            其具有均匀的颗粒形貌和微孔结构。可见光成功诱                                 of Organic Chemistry (有机化学), 2012, 32(12): 2248-2264.
            导苄胺转化成 N-亚苄基苄胺,表明其对于 C—N 键                         [11]  ZHUANG C F (庄长福), LIU J L (刘建路), DAI W (戴文). Synthesis
                                                                   and applications in catalysis of porphyrinic metal-organic frameworks[J].
            的氧化具有催化活性。可见光诱导二苄胺硫醚的氧                                 Progress in Chemistry (化学进展), 2014, 26(Z1): 277-292.
                                                               [12]  LI Z (李臻), JING Z  Q (景震强), XIA C G (夏春谷). Review  on
            化和双胺基缩硫酮的断裂表明其对于 C—S 键的氧                               application of metalloporphyrins  in catalytic oxidation  reactions[J].
                                                                   Chinese Journal of Organic Chemistry (有机化学), 2007, 27(1): 34-44.
            化具有催化活性。相较于卟啉单体,聚卟啉具有更                             [13]  ZHANG J L, CHE C M. Soluble polymer-supported ruthenium porphyrin
            高的光催化活性,筛选出来的 PPOP-1 经 4 次循环                           catalysts for epoxidation, cyclopropanation, and aziridination of
                                                                   alkenes[J]. Organic Letters, 2002, 4(11): 1911-1914.
            后催化活性仍未降低。                                         [14]  YANG F, GAO S Y, XIONG C R, et al. Coordination of manganese
                                                                   porphyrins on amino-functionalized MCM-41 for heterogeneous
                 后续将继续探索聚卟啉对于 C—C、C—O 键氧                           catalysis of naphthalene hydroxylation[J]. Chinese Journal of Catalysis,
                                                                   2015, 36(7): 1035-1041.
            化的催化活性,拓宽其催化的普适性。                                  [15]  JIANG X, GOU F L, CHEN F J, et al. Cycloaddition of epoxides and
                                                                   CO 2  catalyzed by  bisimidazole-functionalized porphyrin cobalt(Ⅲ)
            参考文献:                                                  complexes[J]. Green Chemistry, 2016, 18(12): 3567-3576.
                                                               [16]  CHEN  R F, SHI J L, MA  Y,  et al.  Designed synthesis of a 2D
                                                                               2
            [1]   SHI N (史娜), REN Q G (任清刚), LI  G L  (李观亮). Progress  in   porphyrin-based sp  carbon-conjugated covalent organic framework
                 synthesis of metalloporphyrins and their catalytic oxidation mechanism[J].   for heterogeneous photocatalysis[J]. Angewandte Chemie International
                 Shandong Chemical Industry (山东化工), 2019, 48(14): 90-91.   Edition, 2019, 58(19): 6430-6434.
            [2]   LIU C L (刘长玲), ZHANG M (张明), SONG Y (宋岩). Study on   [17]  LI Y J, SUN B S, ZHOU Y R, et al. Novel conjugated nanoporous
                 photogradation  of  methylene blue with temperature sensitive metal   alkynyl metalloporphyrin framework as effective catalyst for oxidation
                 porphyrin photosentizer[J]. Chemical World (化学世界), 2015, 56(9):   of toluene with molecular oxygen[J]. Applied Organometallic
                 526-528, 533.                                     Chemistry, 2017, 31(3): e3578.
            [3]   SHEN W R (沈伟韧), ZHAO W K (赵文宽), HE F (贺飞),et al. TiO 2-   [18]  OLAVARRIA-CONTRERAS I J, PERRIN M L, CHEN  Z, et al.
                 based photocatalysis and its applications for waste water treatment[J].   C-Au covalently bonded molecular junctions using nonprotected
                 Progress in Chemistry (化学进展), 1998, 10(4): 3-15.   alkynyl anchoring groups[J]. Journal  of the American  Chemical
            [4]   ZHANG J W (张佳玮), MA Z Y (马志远), ZHAO C Z (赵传壮),    Society, 2016, 138(27): 8465-8469.
                 et al. Porphyrin-based derivatives and polymeric  materials[J]. Acta   [19]  WANG  Y Q, LI C J, DU  L B,  et al. A reactive oxygen species-
                 Polymerica Sinica (高分子学报), 2018, 49(7): 864-877.   responsive dendrimer with low cytotoxicity for efficient and targeted
            [5]   MENG A N (孟爱娜). Singlet oxygen mediated metalporphyrin organic   gene delivery[J]. Chinese Chemical Letters, 2020, 31(1): 275-280.
                 framework material for efficient removal of pollutants and kinetic   [20]  WU W (吴伟), QIN Y S (秦玉升), WANG X H (王献红). Bifunctional
                 study[D]. Nanjing: Nanjing Normal University (南京师范大学), 2017.   aluminum porphyrin catalysts for copolymerization of CO 2 and epoxides[J].
            [6]   DONG  R A (董润安), QIU Y (邱勇), SONG X  Q (宋心琦).    Acta Polymerica Sinica (高分子学报), 2014, 45(7): 1017-1022.
                 Photosensitized oxidation  of  biomolecules by porphyrine-like   [21]  ALONSO-CASTRO A J, ZAPATA-MORALES J R, HERNÁNDEZ-
                 compounds[J]. Progress in Chemistry (化学进展), 1998, 10(1): 45-54.   MUNIVE A, et al.  Synthesis, antinociceptive and  anti-inflammatory
            [7]   WU D (吴迪), SHEN Z (沈珍), XUE Z L (薛兆历), et al. Applications   effects  of  porphyrins[J]. Bioorganic & Medicinal Chemistry, 2015,
                 of porphyrin-based sensitizer in dye sensitized solar cell[J]. Chinese   23(10): 2529-2537.
   120   121   122   123   124   125   126   127   128   129   130