CN106995404A - 一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶及制备方法 - Google Patents
一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶及制备方法 Download PDFInfo
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- dihydroxyphenyl
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- MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical group C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 title claims abstract description 44
- RAIOQXXWEGZKAI-UHFFFAOYSA-N 4-[9-(3,4-dihydroxyphenyl)fluoren-9-yl]benzene-1,2-diol Chemical class C1=C(O)C(O)=CC=C1C1(C=2C=C(O)C(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 RAIOQXXWEGZKAI-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 230000005496 eutectics Effects 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 230000015572 biosynthetic process Effects 0.000 title abstract description 7
- 239000013078 crystal Substances 0.000 claims abstract description 45
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000010992 reflux Methods 0.000 claims abstract description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 238000002425 crystallisation Methods 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 238000001816 cooling Methods 0.000 claims abstract description 3
- 239000000706 filtrate Substances 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000002244 precipitate Substances 0.000 claims description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 2
- -1 3,4-dihydroxyphenyl Chemical group 0.000 claims 1
- HFKFGGSWJJXCHQ-UHFFFAOYSA-N 4-[1-(3,4-dihydroxyphenyl)-9H-fluoren-2-yl]benzene-1,2-diol Chemical compound OC=1C=C(C=CC=1O)C1=C(C=2CC3=CC=CC=C3C=2C=C1)C1=CC(=C(C=C1)O)O HFKFGGSWJJXCHQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 1
- 150000003222 pyridines Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000001914 filtration Methods 0.000 description 3
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 241000272171 Scolopacidae Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/127—Preparation from compounds containing pyridine rings
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- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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Abstract
本发明涉及一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶共晶的制备方法。所述共晶结构特征为不对称晶胞中含有由1.5个9,9—双(3,4—二羟基苯基)芴分子与3个4,4’—联吡啶分子，在晶体结构中，1个9,9—双(3,4—二羟基苯基)芴分子上4个羟基通过O‑H···N的氢键作用连接4个不同的4,4’—联吡啶分子，同时这4个4,4’—联吡啶分子再通过O—H···N的氢键连接另外4个不同的9,9—双(3,4—二羟基苯基)芴分子，按照上述方式连接，形成网格结构。制备方法是以乙腈和三氯甲烷为溶剂，采用先加热回流再冷却结晶方式制备得到。本发明提供了多元酚与吡啶类物质形成共晶的制备方法，为该类药物共晶制备提供理论指导意义。
Description
技术领域
本发明属于多酚类化合物与含吡啶类化合物形成共晶的技术领域，具体涉及到一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶及制备方法。
背景技术
共晶最近二十多年来受到广泛的关注。第一个共晶是1844年WÖhler制备了氢醌共晶，并进行了结构表征，但是并没有从理论上给出概念。后来，1967年Schmidt和Snipes两人最先用“共晶”这个词来描述嘧啶和嘌呤的复合物分子。自此以后，共晶概念一直在不断的更新含义，直到2003年，一个较为普遍的接受概念就是共晶作为一种同相的结晶材料，它含有化学计量的两种或者两种以上的中性组份。
超分子化学和晶体工程概念认为共晶是各组分通过氢键或卤键而形成的一种超分子自组装体系，是热力学、动力学和分子识别三者之间相互作用而达到平衡的一个最稳定的结果。对近100多年所制备的共晶的研究发现，共晶的形成作用力主要来自于氢键、卤键、π-π堆积作用和电荷交换等作用力。研究发现，共晶结构中各组份之间不单单只存在一种作用力，而是由各种不同的作用力共同发挥作用，达到平衡后形成稳定的晶体。
共晶作为一个较新的研究领域，目前依然遇到不少挑战。首先遇到的挑战是，对共晶形成的较佳的反应条件和形成机理不能完全掌握，这主要是因为不是任何两种或两种以上组份都能形成共晶，所以必然存在何种组份能够形成结晶以及有多少种组份能够共组装结晶等等问题。这就有必要继续研究有关共晶结晶的方法问题，包括溶剂的选择、结晶方法的选择、组份的选择和化学合成技巧等。
发明内容
本发明的目的是提供一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶及制备方法，为该类药物共晶制备提供理论指导，并对其进行晶体结构测定。
本发明的目的可采用如下技术方案来实现：
一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶，其共晶结构特征为不对称晶胞中含有由1.5个9,9—双(3,4—二羟基苯基)芴分子与3个4,4’—联吡啶分子，在晶体结构中，1个9,9—双(3,4—二羟基苯基)芴分子上4个羟基通过O—H···N的氢键作用连接4个不同的4,4’—联吡啶分子，同时这4个4,4’—联吡啶分子再通过O—H···N的氢键连接另外4个不同的9,9—双(3,4—二羟基苯基)芴分子，按照这样方式无穷连接下去，形成网格结构。
本发明所述的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶属于单斜晶系，空间群为C2/c，晶胞参数为a = 48.713(4) Ǻ，b = 8.5651(7) Ǻ， c = 28.116(2) Ǻ，三个轴角α = 90°，β = 115.7630(10)°，γ = 90°，V = 10564.8(15) Ǻ3。
本发明所述的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶是以乙腈和三氯甲烷为溶剂，采用先加热回流再冷却结晶方式制备得到。具体制备步骤如下：
（1）将摩尔比为2:1~1:2的9,9—双(3,4—二羟基苯基)芴和4,4’—联吡啶加入到圆底烧瓶中，同时加入乙腈溶剂或者三氯甲烷溶剂并放入磁子，体系中溶质总含量比例为1% ~10%；
（2）装上回流装置，搅拌下加热回流，直到溶质完全溶解；
（3）将得到的溶液过滤，滤液在室温下放置，让其自然挥发，数天后析出大量无色晶体；
（4）将析出的晶体过滤，自然晾干得到9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶。
所述的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶的摩尔比为1.5:3。
本发明的有益效果为：本发明提供了多元酚与吡啶类物质形成共晶的制备方法，为该类药物共晶制备提供理论指导意义。
附图说明
图1为9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶不对称结构单元。
图2为9,9—双(3,4—二羟基苯基)芴分子与4,4’—联吡啶分子形成的网格结构图。
具体实施方式
下面结合附图说明本发明的具体实施方式
本发明所选用共晶结晶组份为9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶，溶剂为乙腈或者三氯甲烷。
本发明用到的组份9,9—双(3,4—二羟基苯基)芴，分子式为C25H18O4，其结构式如a所示。组份4,4’—联吡啶，分子式为C10H8N2，其结构式如b所示
不对称晶胞中含有由1.5个9,9—双(3,4—二羟基苯基)芴分子与3个4,4’—联吡啶分子，如图1所示。在晶体结构中，1个9,9—双(3,4—二羟基苯基)芴分子上4个羟基通过O—H···N的氢键作用连接4个不同的4,4’—联吡啶分子，同时这4个4,4’—联吡啶分子再通过O—H···N的氢键连接另外4个不同的9,9—双(3,4—二羟基苯基)芴分子，按照上述方式无穷连接下去，形成网格结构，如图2所示。
本发明所述的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶属于单斜晶系，空间群为C2/c，晶胞参数为a = 48.713(4) Ǻ，b = 8.5651(7) Ǻ， c = 28.116(2) Ǻ，三个轴角α = 90°，β = 115.7630(10)°，γ = 90°，V = 10564.8(15) Ǻ3。
本发明得到的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶是以乙腈和三氯甲烷为溶剂，采用先加热回流再冷却结晶方式制备得到。具体制备步骤如下实施例：
实施例1
将1.0 mmol 9,9—双(3,4—二羟基苯基)芴（382毫克）、1.0 mmol 4,4’—联吡啶（156毫克）置于50 mL圆底烧瓶中，两者的摩尔比为1:1，再加入30 mL乙腈，固体占体系总质量的2%。放入一个磁子，装上回流冷凝管，搅拌下加热回流1小时，趁热过滤，滤液放置在室温下让其自然挥发，数天后从滤液中析出大量无色晶体，过滤，得到分子式为C67.5H51N6O6共晶，称重质量为319.2毫克，产率为92%。
9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶表征过程如下：
（1）9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成共晶的晶体结构测定
选取大小合适晶型较好的晶体粘于一根玻璃丝上，放在Bruker SMART ApexII单晶衍射仪上进行单晶结构测定： 23℃下，以MoK a (λ= 0.71073 Å)射线作为光源，石墨作为单色器，检测面板为Bruker Smart CCD，采用ω扫描方式对晶胞进行扫描测定，并收集衍射强度数据。首先采用BrukerAPEX-II 程序对采集好的数据进行晶胞精修、数据的吸收校正以及还原；然后通过 SHELXTL 软件中的 XS 程序对还原后的数据采用直接法解析结构，获得所有非氢原子的初始相位角，各向异性参数的精修则通过SHELXL-97 程序运行，使用全矩阵最小二乘法，直至数据收敛，最终对非氢原子坐标的进行确定。芳香环上与碳原子相连的氢以及氧原子上的氢原子均通过理论计算法加入。详细的晶体测试参数如下表所示：
| Chemical formula | C67.5H51N6O6 |
| Formula weight | 1042.14 |
| Crystal system | Monoclinc |
| Space group | C2/c |
| a/Å | 48.713(4) |
| b/Å | 8.5651(7) |
| c/Å | 28.116(2) |
| α/° | 90 |
| β/° | 115.7630(10) |
| γ/° | 90 |
| Volume/Å3 | 10564.8(15) |
| Z | 8 |
| D calc/g cm-3 | 1.310 |
| μ/mm-1 | 0.085 |
| T/K | 296(2) |
| Reflns. Collected | 39203 |
| Unique reflns | 9834 |
| R int | 0.0511 |
| Goodness-of-fit | 0.999 |
| R 1(I > 2σ) | 0.0469 |
| wR 2(I>2σ ) | 0.1046 |
（2）9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成共晶的元素分析测试
使用意大利产的Flash EA-2000元素分析仪对9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶进行元素分析，测试表明C、N、H三元素的测定值与理论值相近，其测试结果数据如下：对分子式为C67.5H51N6O6的共晶分析，其理论值为：C 77.79, H 4.93, N 8.06;实测值：C 78.03, H 5.08, N 8.01.
实施例2
将2.0 mmol 9,9—双(3,4-二羟基苯基)芴（764毫克）、1.0 mmol 4,4’—联吡啶（156毫克）置于50 mL圆底烧瓶中，两者的摩尔比为2:1，再加入30 mL乙腈，固体占体系总质量的4%。放入一个磁子，装上回流冷凝管，搅拌下加热回流1小时，趁热过滤，滤液放置在室温下让其自然挥发，数天后从滤液中析出大量无色晶体，过滤，得到分子式为C67.5H51N6O6共晶，称重质量为312.3毫克，产率为90%。
实施例3
将1.0 mmol 9,9—双(3,4-二羟基苯基)芴（382毫克）、2.0 mmol 4,4’—联吡啶（312毫克）置于50 mL圆底烧瓶中，两者的摩尔比为1:2，再加入30 mL乙腈，固体占体系总质量的3%。放入一个磁子，装上回流冷凝管，搅拌下加热回流1小时，趁热过滤，滤液放置在室温下让其自然挥发，数天后从滤液中析出大量无色晶体，过滤，得到分子式为C67.5H51N6O6共晶，称重质量为666.2毫克，产率为96%。
实施例4
将1.0 mmol 9,9—双(3,4-二羟基苯基)芴（382毫克）、2.0 mmol 4,4’—联吡啶（312毫克）置于50 mL圆底烧瓶中，两者的摩尔比为1:2，再加入15 mL乙腈，固体占体系总质量5.6%。放入一个磁子，装上回流冷凝管，搅拌下加热回流1小时，趁热过滤，滤液放置在室温下让其自然挥发，数天后从滤液中析出大量无色晶体，过滤，得到分子式为C67.5H51N6O6共晶，称重质量为659.3毫克，产率为95%。
实施例5
将1.0 mmol 9,9—双(3,4—二羟基苯基)芴（382毫克）、1.0 mmol 4,4’—联吡啶（156毫克）置于50 mL圆底烧瓶中，两者的摩尔比为1:1，再加入20 mL三氯甲烷，固体占体系总质量1.8%。放入一个磁子，装上回流冷凝管，搅拌下加热回流0.5小时，趁热过滤，滤液放置在室温下让其自然挥发，24小时后从滤液中析出大量无色晶体，过滤，得到分子式为C67.5H51N6O6共晶，称重质量为329.7毫克，产率为95%。
实施例6
将2.0 mmol 9,9—双(3,4—二羟基苯基)芴（764毫克）、1.0 mmol 4,4’—联吡啶（156毫克）置于50 mL圆底烧瓶中，两者的摩尔比为2:1，再加入20 mL三氯甲烷，固体占体系总质量3.0%。放入一个磁子，装上回流冷凝管，搅拌下加热回流0.5小时，趁热过滤，滤液放置在室温下让其自然挥发，24小时后从滤液中析出大量无色晶体，过滤，得到分子式为C67.5H51N6O6共晶，称重质量为315.8毫克，产率为91%。
实施例7
将1.0 mmol 9,9—双(3,4—二羟基苯基)芴（382毫克）、2.0 mmol 4,4’—联吡啶（312毫克）置于50 mL圆底烧瓶中，两者的摩尔比为1:2，再加入20 mL三氯甲烷，固体占体系总质量2.3%。放入一个磁子，装上回流冷凝管，搅拌下加热回流0.5小时，趁热过滤，滤液放置在室温下让其自然挥发，24小时后从滤液中析出大量无色晶体，过滤，得到分子式为C67.5H51N6O6共晶，称重质量为673.2毫克，产率为97%。
Claims (4)
1.一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶，其特征是：所述共晶结构特征为不对称晶胞中含有1.5个9,9—双(3,4—二羟基苯基)芴分子与3个4,4’—联吡啶分子，在晶体结构中，1个9,9—双(3,4—二羟基苯基)芴分子上4个羟基通过O—H···N的氢键作用连接4个不同的4,4’—联吡啶分子，同时这4个4,4’—联吡啶分子再通过O—H···N的氢键连接另外4个不同的9,9—双(3,4—二羟基苯基)芴分子，按照上述方式连接，形成网格结构。
2.根据权利要求1所述的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶，其特征在于：所制得的共晶属于单斜晶系，空间群为C2/c，晶胞参数为a = 48.713(4) Ǻ，b= 8.5651(7) Ǻ， c = 28.116(2) Ǻ，三个轴角α = 90°，β = 115.7630(10)°，γ = 90°，V= 10564.8(15)Ǻ3。
3.一种如权利要求1所述的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶制备方法，其特征是采用溶液先回流加热再冷却结晶方法，具体步骤如下：
（1）将9,9—双(3,4—二羟基苯基)芴和4,4’—联吡啶按2:1~1:2的摩尔比加入到圆底烧瓶中，再加入乙腈溶剂或者三氯甲烷溶剂并放入磁子，加入的溶剂量使得体系中溶质总含量比例为1.0% ~10.0%；
（2）装上回流装置，搅拌下加热回流，直到溶质完全溶解；
（3）将得到的溶液过滤，滤液在室温下放置，让其自然挥发，数天后析出大量无色晶体；
（4）将析出的晶体过滤，自然晾干得到9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶。
4.根据权利要求3所述的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶制备方法，其特征是：所述的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶的摩尔比为1.5:3。
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