CN111620899B - 一种苯并硼氮萘噻吩衍生物的合成方法 - Google Patents
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- 238000010189 synthetic method Methods 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- -1 benzo boron nitrogen naphthalene thiophene derivative Chemical class 0.000 claims abstract description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 8
- 238000001308 synthesis method Methods 0.000 claims abstract description 5
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims abstract description 4
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims abstract description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 14
- 238000004440 column chromatography Methods 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 claims 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
- KVKXVUQGGPEISU-UHFFFAOYSA-N BrC1=C(C2=CC=CC=C2C=C1)[N+](=O)[O-].[B] Chemical compound BrC1=C(C2=CC=CC=C2C=C1)[N+](=O)[O-].[B] KVKXVUQGGPEISU-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 7
- 239000011734 sodium Substances 0.000 abstract description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract description 5
- 159000000011 group IA salts Chemical class 0.000 abstract description 4
- 239000003446 ligand Substances 0.000 abstract description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 abstract description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 abstract description 2
- YGLAOZWGTXPVGW-UHFFFAOYSA-M C1=CC=C(C=CC=C2)C2=C1.[B+3].N.[Br-] Chemical group C1=CC=C(C=CC=C2)C2=C1.[B+3].N.[Br-] YGLAOZWGTXPVGW-UHFFFAOYSA-M 0.000 abstract description 2
- OJFINWZQBIXQCP-UHFFFAOYSA-K C1=CC=C(C=CC=C2)C2=C1.[B+3].N.[Br-].[Br-].[Br-].Br.Br.Br Chemical compound C1=CC=C(C=CC=C2)C2=C1.[B+3].N.[Br-].[Br-].[Br-].Br.Br.Br OJFINWZQBIXQCP-UHFFFAOYSA-K 0.000 abstract description 2
- NEEFWCPMRBZKRO-UHFFFAOYSA-N C1=CC=CC2=CC=CC=C12.[N].Br[B] Chemical compound C1=CC=CC2=CC=CC=C12.[N].Br[B] NEEFWCPMRBZKRO-UHFFFAOYSA-N 0.000 abstract description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 abstract description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 abstract description 2
- PENAXHPKEVTBLF-UHFFFAOYSA-L palladium(2+);prop-1-ene;dichloride Chemical compound [Pd+]Cl.[Pd+]Cl.[CH2-]C=C.[CH2-]C=C PENAXHPKEVTBLF-UHFFFAOYSA-L 0.000 abstract description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 abstract description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical group [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 abstract description 2
- 235000011056 potassium acetate Nutrition 0.000 abstract description 2
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 abstract description 2
- 229910052708 sodium Inorganic materials 0.000 abstract description 2
- 238000003912 environmental pollution Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 12
- 229910052786 argon Inorganic materials 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- SPNYYHSMEZSFNX-UHFFFAOYSA-N 1,2,3-tribromonaphthalene Chemical compound C1=CC=C2C(Br)=C(Br)C(Br)=CC2=C1 SPNYYHSMEZSFNX-UHFFFAOYSA-N 0.000 description 1
- DYLNOKDMLRFOBO-UHFFFAOYSA-L C1=CC=C(C=CC=C2)C2=C1.[B+3].N.[Br-].[Br-] Chemical compound C1=CC=C(C=CC=C2)C2=C1.[B+3].N.[Br-].[Br-] DYLNOKDMLRFOBO-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000001897 boron-11 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本发明一种苯并硼氮萘噻吩衍生物的合成方法是以溴代硼氮萘、硫化物、催化剂等为原料,在90‑140℃反应8‑24h后,经浓缩、纯化,得到苯并硼氮萘噻吩衍生物;溴代硼氮萘为硼氮萘单溴代物或双溴代物;硫化物为S8、K2S、Na2S或KSCN;催化剂为醋酸钯、二三苯基膦二氯化钯、[1,1‑双(二苯基磷)二茂铁]二氯化钯、氯化烯丙基钯(II)二聚物或碘化亚铜;配体为三苯基磷,2‑(二叔丁基膦)联苯、2,2'‑二吡啶、4,4'‑二叔丁基‑2,2'‑二吡啶或1,10‑菲罗啉;碱性盐为碳酸钠、碳酸钾、醋酸钾或叔丁醇钠。本发明方法具有反应条件温和,原料适用范围广,反应专一,产率高,环境污染小等优点。
Description
技术领域
本发明涉及一种苯并硼氮萘噻吩衍生物的合成方法,属于有机合成技术领域。
背景技术
硼氮杂稠环分子在有机电子学中的应用研究虽然刚刚起步,这类分子已经展现出了较好的器件性能。目前该材料的种类和数量还较少,导致构效关系的研究较为困难。尽管可以借助理论化学来预测硼氮杂稠环结构的分子轨道和相关性质,明确BN单元共价嵌入后对有机π 共轭材料的电子学性质影响仍需合成大量结构来总结规律。虽然经历了近60 年的努力,硼氮杂芳香稠环化合物的合成仍然是有机合成中的一个难题,将BN单元共价嵌入共轭结构中的高效合成方法还较少,除了比较常用的亲电取代反应,虽然不断有新的合成路线被提出,但它们的适用性都相对较窄。合成上的难度限制了这类材料进一步应用于有机电子学领域。因此,不断发展高效合成硼氮杂芳香稠环化合物的新方法对于此类材料的研究及应用具有重要的意义。
发明内容
本发明的目的是提供一种原料广泛、反应简单、反应专一性强、产率高的苯并硼氮萘噻吩衍生物的合成方法。
本发明采用以下技术方案来实现上述目的,本发明一种苯并硼氮萘噻吩衍生物的合成方法过程为:将溴代硼氮萘、硫化物、催化剂、配体和碱性盐加入到Schlenk瓶中,抽真空换氮气,再加入溶剂,然后反应体系升温到60~140℃,反应8-24h;产物分别经减压除去溶剂、柱层析,得到苯并硼氮萘噻吩衍生物;其中,硫化物的用量为溴代硼氮萘摩尔量的1~3倍,催化剂的用量为溴代硼氮萘摩尔量的1%~10 %,配体的用量为溴代硼氮萘摩尔量的2%~20%,碱性盐的用量为溴代硼氮萘摩尔量的1~6倍,溶剂的用量为每摩尔溴代硼氮萘5L的比例。
所述的溴代硼氮萘为硼氮萘单溴代物或硼氮萘二溴代物。
所述的硫化物为S8、K2S、Na2S或KSCN。
所述的催化剂为醋酸钯、二三苯基膦二氯化钯、[1,1-双(二苯基磷)二茂铁]二氯化钯、氯化烯丙基钯(II)二聚物或碘化亚铜。
所述的配体为三苯基磷、2-(二叔丁基膦)联苯、2,2'-二吡啶、4,4'-二叔丁基-2,2'-二吡啶或1,10-菲罗啉。
所述的碱性盐为碳酸钠、碳酸钾、醋酸钾或叔丁醇钠。
所述的溶剂为甲苯,四氢呋喃或二甲基甲酰胺。
苯并硼氮萘噻吩衍生物反应方程式为:
本发明的有益效果:以溴代硼氮萘、硫化物,用钯或铜作为催化剂,一步合成苯并硼氮萘噻吩衍生物,反应简单,条件温和,反应专一性强,产率高,催化剂无毒环保,价格便宜,原料范围广泛,反应过程对环境的影响小。
具体实施方式
下面结合典型实施例来进一步描述本发明:
实施例1
取15 mL干燥的Schlenk管,抽真空换氩气3次,氩气保护下,依次加入双溴代硼氮萘 (362 mg, 1 mmol),Na2S (156 mg, 2 mmol), CuI (19 mg, 10 mol %), 4,4'-二叔丁基-2,2'-二吡啶(54 mg,20 mol %)Na2CO3 (160 mg, 1.5 mmol),导入无水无氧溶剂DMF (5mL)。氩气保护下,120℃反应约8 h,反应结束,待体系温度降至室温后,二氯甲烷(4*10 mL)和水(50 mL)萃取,合并有机相,无水硫酸钠干燥后,减压除去溶剂,柱层析分离(展开剂:正己烷:二氯甲烷=5:1),得黄绿色固体160 mg,收率68%。
1H NMR图谱、13C、11B NMR图谱用Bruker公司生产的400兆超导核磁仪,用氘代氯仿作为溶剂,TMS作为参比进行测定。
该化合物的核磁分析数据如下:
1H NMR (400 MHz, CDCl3): δ 8.47 (1H, s, NH), 8.22 (1H, s), 8.03 (1H,d, J = 8 Hz), 7.73 (2H, t, J = 8 Hz), 7.44-7.53 (3H, m), 7.23-7.54 (2H, m).13C NMR (101 MHz, CDCl3): δ 154.5 (s, quaternary-C), 137.7 (s, quaternary-C),133.4, 131.2, 130.9, 128.7, 127.3, 125.7 (s, quaternary-C), 123.7, 123.5,121.6, 118.9。与硼原子相连的碳无信号响应。
实施例2
合成苯并硼氮萘噻吩衍生物化合物2:
取15 mL干燥的Schlenk管,抽真空换氩气3次,氩气保护下,依次加入单溴代硼氮萘 (297 mg, 1 mmol),Na2S (156 mg, 2 mmol), CuI (19 mg, 10 mol %), 4,4'-二叔丁基-2,2'-二吡啶(54 mg,20 mol %), Na2CO3 (160 mg, 1.5 mmol),导入无水无氧溶剂四氢呋喃 (5 mL)。氩气保护下,140℃反应约6 h,反应结束,待体系温度降至室温后,二氯甲烷(4*10 mL)和水(50 mL)萃取,合并有机相,无水硫酸钠干燥后,减压除去溶剂,柱层析分离(展开剂:正己烷:二氯甲烷=5:1),得黄绿色固体181 mg,收率72%。
该化合物的核磁分析数据如下:
1H NMR (400 MHz, CDCl3): δ 8.35 (1H, s, NH), 8.27(1H, s), 7.87 (1H,d, J = 8 Hz), 7.73 (2H, t, J = 8 Hz), 7.43-7.66 (3H, m), 7.31-7.54 (1H, m),2.42 (s, CH3). 13C NMR (101 MHz, CDCl3): δ 143.9 (s, quaternary-C), 137.7 (s,quaternary-C), 133.4, 131.2, 130.9, 128.7, 127.3, 125.7 (s, quaternary-C),123.7, 123.5, 121.6, 118.9, 24.5。与硼原子相连的碳无信号响应。
实施例3
合成苯并硼氮萘噻吩衍生物化合物3:
取15 mL干燥的Schlenk管,抽真空换氩气3次,氩气保护下,依次加入单溴代硼氮萘 (301mg, 1 mmol),Na2S (156 mg, 2 mmol), CuI (19 mg, 10 mol %), 2,2'-二吡啶(32 mg,20 mol %), Na2CO3 (160 mg, 1.5 mmol),导入无水无氧溶剂四氢呋喃 (5 mL)。氩气保护下,100℃反应约18 h,反应结束,待体系温度降至室温后,二氯甲烷(4*10 mL)和水(50 mL)萃取,合并有机相,无水硫酸钠干燥后,减压除去溶剂,柱层析分离(展开剂:正己烷:二氯甲烷=5:1),得黄绿色固体178 mg,收率70%。
该化合物的核磁分析数据如下:
1H NMR (400 MHz, CDCl3): δ 8.37 (1H, br s, NH), 8.13 (1H, d, J = 12Hz), 7.66 (1H, d, J = 8.0 Hz), 7.58 (1H, t, J = 8.0 Hz), 7.44 (1H, t, J = 8.0Hz), 7.36 (1H, d, J = 8.0 Hz), 7.21 (1H, t, J = 8.0 Hz), 7.06-7.13 (2H, m).13C NMR (101 MHz, CDCl3): δ 161.8 (d, JC-F = 253.5 Hz, quaternary-C), 144.3(s, CH), 138.4 (s, quaternary-C), 135.7 (d, JC-F = 8.1 Hz), 128.4 127.5,126.2(d, JC-F = 10.10 Hz, quaternary-C), 124.3 (s, quaternary-C) 120.5, 119.0 (d,JC-F = 23.2 Hz), 117.4, 113.2 (d, JC-F = 19.2 Hz, Ar-C). 与硼相连的碳无信号响应。
Claims (1)
1.一种苯并硼氮萘噻吩衍生物的合成方法,其特征在于:所述的合成方法过程为:将溴代硼氮萘、硫化钠、碘化亚铜、4,4'-二叔丁基-2,2'-二吡啶和碳酸钠加入到Schlenk瓶中,抽真空换氮气,再加入二甲基甲酰胺,然后反应体系升温到120℃,反应8h;产物分别经减压除去二甲基甲酰胺、柱层析,得到苯并硼氮萘噻吩衍生物;其中,硫化钠的用量为溴代硼氮萘摩尔量的2倍,碘化亚铜的用量为溴代硼氮萘摩尔量的10 %,4,4'-二叔丁基-2,2'-二吡啶的用量为溴代硼氮萘摩尔量的20%,碳酸钠的用量为溴代硼氮萘摩尔量的1.5倍,二甲基甲酰胺的用量为每摩尔溴代硼氮萘5L的比例;
所述的溴代硼氮萘为3-溴-2-(2-溴代苯基)-1,2-硼氮萘,结构式为:
苯并硼氮萘噻吩衍生物为:
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