苯并噻吩螺烯的合成与晶体结构的研究
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摘要
并噻吩螺烯化合物由于其共轭和手性的完美结合,在有机光电领域有广泛的应用背景,引起了人们受到了越来越多的关注。本文尝试通过化学和光化学方法合成多种苯并噻吩(螺烯)化合物,并对它们的晶体结构及相关的光谱进行了研究,具体的研究内容主要包括以下四个方面：
1. [7]苯并六噻吩螺烯的合成研究与晶体结构
1.1 2,11-二辛基-[7]苯并六噻吩螺烯的光化学合成与晶体结构
通过以下路线探索合成出了2,11-二辛基-[7]苯并六噻吩螺烯(12)：1)二噻吩并[2,3-b：3',2'-d]噻吩(5)通过LDA夺质子,溴辛烷烷基化得到2-辛烷基二噻吩并[2,3-b：3’,2’-d]噻吩(6)(产率：33.8%)；2)化合物6经过LDA夺质子,N,N-二甲基甲酰胺(DMF)醛基化得到化合物5-辛基二噻吩并[2,3-b：3',2'-d]噻吩-2-醛(7)(产率：97.9%)；3)化合物7进行McMurry反应,得到二(2-辛基二噻吩并[2,3-b：3',2’-d]噻吩)乙烯(11)(产率：94.9%)；4)化合物11通过光化学氧化关环合成目标化合物2,11-二辛基-[7]苯并六噻吩螺烯(12)(产率：32.3%)。如果以二噻吩并[2,3-b：3’,2’-d]噻吩(5)为起始原料,总产率为10.2%。12的晶体堆积图显示该螺烯化合物的两种异构体(R)-12和(S)-12存在S…S和π…S相互作用。
1.2 2,11-二(三甲基硅)-[7]苯并六噻吩螺烯的化学合成与晶体结构
通过以下路线探索合成出了2,11-二(三甲基硅)-[7]苯并六噻吩螺烯(22)：1)以5,5’-二(三甲基硅)-3,3’-联(二噻吩并[2,3-b：3’,2’-d]噻吩)(29)为原料,通过LDA夺内侧噻吩α位质子,DMF醛基化得到5,5'-二(三甲基硅基)-3,3’-联(二噻吩并[2,3-b.3,2-d]噻吩)-2,2'-二醛(30)(产率：92.6%)；2)化合物30通过分子内McMurry,反应制备出了2,11-二(三甲基硅)-[7]苯并六噻吩螺烯(22)(产率：42.4%)。以化合物29为原料,生成七元苯并噻吩化合物22的总产率为39.3%。化合物22单晶有两种晶型：正交的Pbca空间群(外观：浅粉色)和三斜的P-1空间群(外观：无色)。两种晶型的晶体堆积图中都存在(R)-22和(S)-22间的S…S,π…S和π…π相互作用。
2.首次合成了萘核噻吩双螺烯化合物,并对其晶体结构进行了研究
以二噻吩并[2,3-b：3’,2’-d]噻吩为建筑块制备了萘核噻吩双螺烯化合物34,化合物34是新颖的两个七元苯并噻吩螺烯稠合的双螺烯手性分子,具备分子美学和功能性双重特点。制备过程：1)化合物5,5'-二(三甲基硅)-3,3’-联(二噻吩并[2,3-b：3',2'-d]噻吩)(29)经强碱LDA夺质子,N,N-二甲氨基甲酰氯(DMC)关环得到二[5,5’-二(三甲基硅)-3,3’-联二噻吩并[2,3-b：3’,2’-d]噻吩]-2,2’-二酮(39)(产率：49.8%)；2)化合物39通过分子内McMurry,反应合成萘核噻吩双螺烯(34)：5,5',5'',5'''-四(三甲基硅)-萘并[1,2-b：3,4-b':5,6-b'':7,8-b''']四(二噻吩并[2,3-b：3’,2’-d]噻吩)(产率：80.1%)。以5,5'-二(三甲基硅)-3,3’-联(二噻吩并[2,3-b：3,2-d]噻吩)(29)为原料,合成萘核噻吩双螺烯(34)的总产率达到39.9%.
化合物34是一种手性交叉共轭的双螺旋化合物,其结构十分独特。34的晶体属正交晶系,P212121空间群。其晶体中(R,R)-34与(S,S)-34因S…S和π…S相互作用而成对单元出现,堆积图显示分子间存在S…S,π…S和π…π相互作用。3.1,1,2,2-四(5-三甲基硅-二噻吩并[2,3-b：3’,2’-d]噻吩-2-)乙烯(36)的合成和聚集诱导发光现象研究
以二噻吩并[2,3-b：3’,2’-d]噻吩为建筑块制备了1,1,2,2-四(5-三甲基硅-二噻吩并[2,3-b：3’,2’-d]噻吩-2-)乙烯(36),以化合物27为起始原料,合成化合物36的总产率为16.7%。
通过对化合物36在四氢呋喃和水混合溶剂以及固态薄膜状态下的光谱行为进行研究,结果表明化合物36是新的一类低聚稠合噻吩基的聚集诱导发光分子；通过溶剂效应、粘度效应以及温度效应,证明分子内单键旋转受阻是导致化合物36聚集诱导发光现象产生的原因；化合物36在四氢呋喃和水混合溶剂,77K和甘油和甲醇混合溶剂不同情况下,分别发出绿色,蓝色和橙色三种颜色的光。
4.Δ7,7'-双环戊[1,2-b：4,3-b']并二噻吩(41)的合成与晶体结构
以2,2'-二溴-5,5’-二-(三甲基硅基)-[3,3’]联噻吩(3)为原料探索出了合成具有低带隙的导电聚合物单体Δ7,7'-双环戊[1,2-b：4,3-b']并二噻吩(41)的有效方法。以化合物3为起始原料,合成化合物41的总产率为50.9%。化合物(TMS)4-41的晶体属单斜晶系,C2／c空间群。(TMS)4-41的晶体结构具备以下特点：(1)分子具有近平面结构；(2)键长趋于平均化。这些特点说明分子具有较强的共轭效应。
The synthesis and characterization of thiophene fusedπ-conjugated molecules and polymers are of current interest owing to their potential applications in organic optoelectronic materials and devices. The heterohelicenes with thiophene units fused in the polyaromatic rings show attactive molecular structures with aesthetics. The synthesis of such kind of benzothiahelicenes is very challenged and attracted to many organic chemists. In this dissertation, the efficient synthesis of several kind of benzothiahelicenes has been developed by using the photocylization and non-photochemical synthetic methodologies. The research work is composed of four parts:
1. Syntheses and Crystal Structures of Benzohexathia[7]helicene
1.1 Synthesis of 2, 11-Dioctylbenzohexathia[7]helicene (12) under Irradiation and its Crystal Structure
12 could be prepared in four steps with dithieno[2,3-b:3',2'-d]thiophene (5) as starting material (Scheme 1).1) 5 was treated with LDA and quenching with 1-bromooctane to give 2-octyldithieno[2,3-b:3',2'-d]thiophene (6) in 33.8% yield. 2-octyldithieno[2,3-b:3',2'-d] thiophene-2-carbaldehyde (7) was made in 97.9% yield by using 6 treated with LDA and quenching with DMF. The McMurry reaction was employed in making 1,2-(5-octyldithieno-[2,3-b:3',2'-d]thiophen-2-yl)-ethene (11) in 94.9%. Finally, the photocyclization of 11 in the presence of iodine in dry benzene was empolyed in making 12 in 32.3% yield. The total yield of making 12 was 10.2% with 5 as starting material. Rac-12 crystallizes in monoclinic, space group P2(1)/n. In the crystal, the strongπ…S and S…S interactions between two enantiomers, (R)-12 and (S)-12 could be observed.
1.2 Synthesis of 2,11-Di(trimethylsilanyl)-benzohexathia[7]helicene (22) and its Crystal Structure
5,5'-di(trimethylsilanyl)-3,3'-bis-dithieno[2,3-b:3',2'-d]thiophene (29) was treated with LDA and DMF to generate 5,5'-di(trimethylsilanyl)-3,3'-bis-dithieno[2,3-b:3',2'-d]-thiophene-2,2'-dialdehyde (30) in 92.6% yield. The intramolecular McMurry reaction was employed in making 2,11-di(trimethylsilanyl)-benzohexathia[7]helicene (22) in 42.4% yield. The total yield of making 22 was 39.3% with 29 as starting material (Scheme 2). Slow evaporation of solution of 1 in a mixture of solvents of CHCl3 and CH3OH (1:3, v/v), two kind of crystals of 1 were obtained at same time. One with slight pink belongs to orthorhombic Pbca space group and another one is colourless, shows triclinic P-1 space group. The S…S,π…S andπ…πinteractions are observed in both crystals between (R)-22 and (S)-22.
2. Synthesis of Novel Naphthalene Cored Double Hexathia[7]helicene and its crystal structure
The efficient synthesis of highlyπ-extended naphthalene cored double helicence, 5,5',5",5'''-tetra(trimethylsilyl)-naphtho[1,2-b:3,4-b':5,6-b":7,8-b''']tetra(dithieno[2,3-b :3',2'-d]-thiophene) (34) was obtained in our work with dithieno[2,3-b:3',2'-d]-thiophene (DTT) as building block.29 was treated with LDA and DMC to afford an novel ten membered cyclic diketone, a dimer of bis(5-trimethylsilanyldithieno-[2,3-b;3',2'-d]thiophen-2-yl)-methanone (39). The intramolecular McMurry reaction of 39 was employed to obtain the naphthalene cored double helicene, rac-34 in 80.1% yield. The total yield of making 34 was 39.9% with 29 as starting material (Scheme 3).34 is a novel compound bearing four twist DTT arms with double helical structure. It crystallizes in the orthorhombic, P212121 space group.34 shows strong The S…S,π…S andπ…πinteractions between (R,R)-34 and (S,S)-34. In addition, the diketone,39 also shows somewhat of double-helix like conformation and crystallizes in triclinic, P-1 space group.
3. Synthesis and Aggregation-Induced Emission Characteristics of 1,1,2,2-tetra (5-trimethylsilyl-dithieno[2,3-b:3',2'-d]thiophene-2-yl)-ethylene(36)
1,1,2,2-Tetra(5-trimethylsilyl-dithieno[2,3-b:3',2'-d]thiophene-2-yl)-ethylene(36) was synthesized by using the 5-bromo-2-trimethylsilanyldithieno[2,3-b:3',2'-d]-thiophene (27) as the starting material. The total yield of making 36 was 16.7% with 27 as starting material.
The fluorescence behaviors of 36 in H2O-THF binary solvent system and in thin film show that 36 is a kind of aggregation-induced emission (AIE)-active compound. It is clearly confirmed by solvent effect, temperature effect and viscosity effect that the restriction of intramolecular C-C bonds rotation plays a crucial role in the AIE process. Some interesting aggregation phenomena of 36 were observed. In H2O-THF binary solvent system,36 emits green light peaked at 500 nm with water fractions of 55-60%. When mediate temperature decreased to 77 k,36 emits yellow light peaked at 560 nm in ethyl ether. However, in glycerol-methanol binary solvent system with glycerol fractions of 30-90% at room temperature,36 emits orange light peaked at 595 nm. The different PL emissions are probably due to different aggregation state.
4. Synthesis and Crystal Structure ofΔ7,7'-dicyclopenta[2,1-b:4,3-b']dithiophene (41)
The total yield of making 41 was 50.9% with 3 as starting material. (TMS)4-41 crystallizes in monoclinic, C2/c space group. It is a planar molecule with high conjugation. The averagement of data of single bonds and double bonds in molecule (TMS)4-41 could be observed from its crystal data.
1. [7]苯并六噻吩螺烯的合成研究与晶体结构
1.1 2,11-二辛基-[7]苯并六噻吩螺烯的光化学合成与晶体结构
通过以下路线探索合成出了2,11-二辛基-[7]苯并六噻吩螺烯(12)：1)二噻吩并[2,3-b：3',2'-d]噻吩(5)通过LDA夺质子,溴辛烷烷基化得到2-辛烷基二噻吩并[2,3-b：3’,2’-d]噻吩(6)(产率：33.8%)；2)化合物6经过LDA夺质子,N,N-二甲基甲酰胺(DMF)醛基化得到化合物5-辛基二噻吩并[2,3-b：3',2'-d]噻吩-2-醛(7)(产率：97.9%)；3)化合物7进行McMurry反应,得到二(2-辛基二噻吩并[2,3-b：3',2’-d]噻吩)乙烯(11)(产率：94.9%)；4)化合物11通过光化学氧化关环合成目标化合物2,11-二辛基-[7]苯并六噻吩螺烯(12)(产率：32.3%)。如果以二噻吩并[2,3-b：3’,2’-d]噻吩(5)为起始原料,总产率为10.2%。12的晶体堆积图显示该螺烯化合物的两种异构体(R)-12和(S)-12存在S…S和π…S相互作用。
1.2 2,11-二(三甲基硅)-[7]苯并六噻吩螺烯的化学合成与晶体结构
通过以下路线探索合成出了2,11-二(三甲基硅)-[7]苯并六噻吩螺烯(22)：1)以5,5’-二(三甲基硅)-3,3’-联(二噻吩并[2,3-b：3’,2’-d]噻吩)(29)为原料,通过LDA夺内侧噻吩α位质子,DMF醛基化得到5,5'-二(三甲基硅基)-3,3’-联(二噻吩并[2,3-b.3,2-d]噻吩)-2,2'-二醛(30)(产率：92.6%)；2)化合物30通过分子内McMurry,反应制备出了2,11-二(三甲基硅)-[7]苯并六噻吩螺烯(22)(产率：42.4%)。以化合物29为原料,生成七元苯并噻吩化合物22的总产率为39.3%。化合物22单晶有两种晶型：正交的Pbca空间群(外观：浅粉色)和三斜的P-1空间群(外观：无色)。两种晶型的晶体堆积图中都存在(R)-22和(S)-22间的S…S,π…S和π…π相互作用。
2.首次合成了萘核噻吩双螺烯化合物,并对其晶体结构进行了研究
以二噻吩并[2,3-b：3’,2’-d]噻吩为建筑块制备了萘核噻吩双螺烯化合物34,化合物34是新颖的两个七元苯并噻吩螺烯稠合的双螺烯手性分子,具备分子美学和功能性双重特点。制备过程：1)化合物5,5'-二(三甲基硅)-3,3’-联(二噻吩并[2,3-b：3',2'-d]噻吩)(29)经强碱LDA夺质子,N,N-二甲氨基甲酰氯(DMC)关环得到二[5,5’-二(三甲基硅)-3,3’-联二噻吩并[2,3-b：3’,2’-d]噻吩]-2,2’-二酮(39)(产率：49.8%)；2)化合物39通过分子内McMurry,反应合成萘核噻吩双螺烯(34)：5,5',5'',5'''-四(三甲基硅)-萘并[1,2-b：3,4-b':5,6-b'':7,8-b''']四(二噻吩并[2,3-b：3’,2’-d]噻吩)(产率：80.1%)。以5,5'-二(三甲基硅)-3,3’-联(二噻吩并[2,3-b：3,2-d]噻吩)(29)为原料,合成萘核噻吩双螺烯(34)的总产率达到39.9%.
化合物34是一种手性交叉共轭的双螺旋化合物,其结构十分独特。34的晶体属正交晶系,P212121空间群。其晶体中(R,R)-34与(S,S)-34因S…S和π…S相互作用而成对单元出现,堆积图显示分子间存在S…S,π…S和π…π相互作用。3.1,1,2,2-四(5-三甲基硅-二噻吩并[2,3-b：3’,2’-d]噻吩-2-)乙烯(36)的合成和聚集诱导发光现象研究
以二噻吩并[2,3-b：3’,2’-d]噻吩为建筑块制备了1,1,2,2-四(5-三甲基硅-二噻吩并[2,3-b：3’,2’-d]噻吩-2-)乙烯(36),以化合物27为起始原料,合成化合物36的总产率为16.7%。
通过对化合物36在四氢呋喃和水混合溶剂以及固态薄膜状态下的光谱行为进行研究,结果表明化合物36是新的一类低聚稠合噻吩基的聚集诱导发光分子；通过溶剂效应、粘度效应以及温度效应,证明分子内单键旋转受阻是导致化合物36聚集诱导发光现象产生的原因；化合物36在四氢呋喃和水混合溶剂,77K和甘油和甲醇混合溶剂不同情况下,分别发出绿色,蓝色和橙色三种颜色的光。
4.Δ7,7'-双环戊[1,2-b：4,3-b']并二噻吩(41)的合成与晶体结构
以2,2'-二溴-5,5’-二-(三甲基硅基)-[3,3’]联噻吩(3)为原料探索出了合成具有低带隙的导电聚合物单体Δ7,7'-双环戊[1,2-b：4,3-b']并二噻吩(41)的有效方法。以化合物3为起始原料,合成化合物41的总产率为50.9%。化合物(TMS)4-41的晶体属单斜晶系,C2／c空间群。(TMS)4-41的晶体结构具备以下特点：(1)分子具有近平面结构；(2)键长趋于平均化。这些特点说明分子具有较强的共轭效应。
The synthesis and characterization of thiophene fusedπ-conjugated molecules and polymers are of current interest owing to their potential applications in organic optoelectronic materials and devices. The heterohelicenes with thiophene units fused in the polyaromatic rings show attactive molecular structures with aesthetics. The synthesis of such kind of benzothiahelicenes is very challenged and attracted to many organic chemists. In this dissertation, the efficient synthesis of several kind of benzothiahelicenes has been developed by using the photocylization and non-photochemical synthetic methodologies. The research work is composed of four parts:
1. Syntheses and Crystal Structures of Benzohexathia[7]helicene
1.1 Synthesis of 2, 11-Dioctylbenzohexathia[7]helicene (12) under Irradiation and its Crystal Structure
12 could be prepared in four steps with dithieno[2,3-b:3',2'-d]thiophene (5) as starting material (Scheme 1).1) 5 was treated with LDA and quenching with 1-bromooctane to give 2-octyldithieno[2,3-b:3',2'-d]thiophene (6) in 33.8% yield. 2-octyldithieno[2,3-b:3',2'-d] thiophene-2-carbaldehyde (7) was made in 97.9% yield by using 6 treated with LDA and quenching with DMF. The McMurry reaction was employed in making 1,2-(5-octyldithieno-[2,3-b:3',2'-d]thiophen-2-yl)-ethene (11) in 94.9%. Finally, the photocyclization of 11 in the presence of iodine in dry benzene was empolyed in making 12 in 32.3% yield. The total yield of making 12 was 10.2% with 5 as starting material. Rac-12 crystallizes in monoclinic, space group P2(1)/n. In the crystal, the strongπ…S and S…S interactions between two enantiomers, (R)-12 and (S)-12 could be observed.
1.2 Synthesis of 2,11-Di(trimethylsilanyl)-benzohexathia[7]helicene (22) and its Crystal Structure
5,5'-di(trimethylsilanyl)-3,3'-bis-dithieno[2,3-b:3',2'-d]thiophene (29) was treated with LDA and DMF to generate 5,5'-di(trimethylsilanyl)-3,3'-bis-dithieno[2,3-b:3',2'-d]-thiophene-2,2'-dialdehyde (30) in 92.6% yield. The intramolecular McMurry reaction was employed in making 2,11-di(trimethylsilanyl)-benzohexathia[7]helicene (22) in 42.4% yield. The total yield of making 22 was 39.3% with 29 as starting material (Scheme 2). Slow evaporation of solution of 1 in a mixture of solvents of CHCl3 and CH3OH (1:3, v/v), two kind of crystals of 1 were obtained at same time. One with slight pink belongs to orthorhombic Pbca space group and another one is colourless, shows triclinic P-1 space group. The S…S,π…S andπ…πinteractions are observed in both crystals between (R)-22 and (S)-22.
2. Synthesis of Novel Naphthalene Cored Double Hexathia[7]helicene and its crystal structure
The efficient synthesis of highlyπ-extended naphthalene cored double helicence, 5,5',5",5'''-tetra(trimethylsilyl)-naphtho[1,2-b:3,4-b':5,6-b":7,8-b''']tetra(dithieno[2,3-b :3',2'-d]-thiophene) (34) was obtained in our work with dithieno[2,3-b:3',2'-d]-thiophene (DTT) as building block.29 was treated with LDA and DMC to afford an novel ten membered cyclic diketone, a dimer of bis(5-trimethylsilanyldithieno-[2,3-b;3',2'-d]thiophen-2-yl)-methanone (39). The intramolecular McMurry reaction of 39 was employed to obtain the naphthalene cored double helicene, rac-34 in 80.1% yield. The total yield of making 34 was 39.9% with 29 as starting material (Scheme 3).34 is a novel compound bearing four twist DTT arms with double helical structure. It crystallizes in the orthorhombic, P212121 space group.34 shows strong The S…S,π…S andπ…πinteractions between (R,R)-34 and (S,S)-34. In addition, the diketone,39 also shows somewhat of double-helix like conformation and crystallizes in triclinic, P-1 space group.
3. Synthesis and Aggregation-Induced Emission Characteristics of 1,1,2,2-tetra (5-trimethylsilyl-dithieno[2,3-b:3',2'-d]thiophene-2-yl)-ethylene(36)
1,1,2,2-Tetra(5-trimethylsilyl-dithieno[2,3-b:3',2'-d]thiophene-2-yl)-ethylene(36) was synthesized by using the 5-bromo-2-trimethylsilanyldithieno[2,3-b:3',2'-d]-thiophene (27) as the starting material. The total yield of making 36 was 16.7% with 27 as starting material.
The fluorescence behaviors of 36 in H2O-THF binary solvent system and in thin film show that 36 is a kind of aggregation-induced emission (AIE)-active compound. It is clearly confirmed by solvent effect, temperature effect and viscosity effect that the restriction of intramolecular C-C bonds rotation plays a crucial role in the AIE process. Some interesting aggregation phenomena of 36 were observed. In H2O-THF binary solvent system,36 emits green light peaked at 500 nm with water fractions of 55-60%. When mediate temperature decreased to 77 k,36 emits yellow light peaked at 560 nm in ethyl ether. However, in glycerol-methanol binary solvent system with glycerol fractions of 30-90% at room temperature,36 emits orange light peaked at 595 nm. The different PL emissions are probably due to different aggregation state.
4. Synthesis and Crystal Structure ofΔ7,7'-dicyclopenta[2,1-b:4,3-b']dithiophene (41)
The total yield of making 41 was 50.9% with 3 as starting material. (TMS)4-41 crystallizes in monoclinic, C2/c space group. It is a planar molecule with high conjugation. The averagement of data of single bonds and double bonds in molecule (TMS)4-41 could be observed from its crystal data.
引文
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