基于红色荧光性能的卟啉化合物的设计、合成与表征
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摘要
本文以卟啉化合物的合成方法及其发光性能研究为目的，设计并合成了三种类型的卟啉目标分子：中位带有取代基的卟啉分子，吡咯β位带有取代基的卟啉分子，中位和吡咯β位全带有取代基的卟啉分子；对合成卟啉分子的光谱性能进行了分析；用卟啉搀杂8-羟基喹啉铝(搀杂质量分数分别为1.5％，2％，2.7％，5％)作为发光层制备了红色有机电致发光器件；通过卟啉液相搀杂8-羟基喹啉铝对红光器件的仿真模拟，找到了一种红光染料的化学筛选方法。具体内容分以下几个部分：
1．三种类型卟啉的合成研究
设计并合成了20种卟啉化合物，即：四甲基四乙基卟啉(TMTE，1)，四甲基四乙基锌卟啉(TMTEZn，2)，八乙基卟啉(OEP，3)，八乙基锌卟啉(OEPZn，4)，四苯基卟啉(TPPH_2，5)，四苯基钴卟啉(TPPCo，6)，四对羟基苯基卟啉(Tp-OHPPH_2，7)，四对氯苯基卟啉(Tp-ClPPH_2，8)，四对甲氧基苯基卟啉(Tp-MeOPPH_2，9)，四(3，4-二甲氧基苯基)卟啉(T_(3,4)-diMeOPPH_2，10)，四对氨基苯基卟啉(TAPPH_2，11)，四苯乙烯基卟啉(TStPPH_2，12)，四联苯基卟啉(TBPPH_2，13)，四[对(对羟基苯偶氮基)]苯基卟啉[Tp-(p-OHBazo)PPH_2，14]，四[对(对羟基邻甲基苯偶氮基)]苯基卟啉[Tp-(p-OH-o-CH_3Bazo)PPH_2，15]，四(对羟基间苯偶氮基)苯基卟啉(Tp-OH-m-BazoPPH_2，16)，四(邻羟基间苯偶氮基)苯基卟啉(To-OH-m-BazoPPH_2，17)，四[对(β羟基萘偶氮基)]苯基卟啉[Tp-(β-OHNazo)PPH_2，18]，八甲基二间溴代苯基二苯基卟啉[(OM-B-m-BrP-BP)PH_2，19]，偶氮二聚卟啉(DiPPH_2，20)。本文共合成了8种取代芳醛：联苯甲醛(21)，对氨基苯甲醛(22)，邻羟基对苯偶氮基苯甲醛(23)，对羟基间苯偶氮基苯甲醛(24)，4-(对羟基苯偶氮基)苯甲醛(25)，4-(邻甲基对羟基苯偶氮基)苯甲醛(26)，4-(β羟基萘偶氮基)苯甲醛(27)，4,4'-二(邻羟基间甲酰基苯偶氮基)联苯(28)。黑体化合物(12，15，16，17，19，20，24，25，26，27，28)为新化合物；(13，14，18)是采用新方法合成的化合物。这些化合物的结构通过了HNMR，MS，UV-Vis，Elemental analysis及IR表征，本部分主要内容如下：
(1)卟啉合成方法的研究
本文通过对Adler法合成装置的改进，即加一吸水装置，使反应平衡右移，以对氨基苯甲醛与吡咯在丙酸中直接缩合合成卟啉(11)，产率提高了9％；反应体系中
在加入模板剂的同时通入NZ，桂皮醛与毗咯在醋酸中缩合合成了四苯乙烯基锌叶
琳，用盐酸脱锌得四苯乙烯基叶啦口段PpH全，12)，对于烯基醛与毗咯直接缩合合
成叶琳的方法未见相关文献报道，是一种新的合成方法;采用醋酸为溶剂，在模板
剂作用下，避光避热，常温搅拌，后期回流的方法合成了[( OM.卜m七fP一巧PHZ，
1外这对于合成光热敏感的化合物具有很好的借鉴意义;采用醋酸为溶剂，用偶氮
醛与毗咯一步缩合合成了系列偶氮叶琳，醋酸是一种合成对称偶氮n卜琳的理想介质;
采用联苯二胺重氮盐与单经基p卜琳在碱性条件下直接偶合，合成了偶氮二聚叶琳，
拓宽了重氮盐与酚的作用范围。
(2)中间体合成研究
利用重氮偶合反应合成了系列芳香偶氮醛，采用抓甲基法成功制备了联苯甲醛，
利用Khorr反应合成了毗咯衍生物，对中间体的合成进行了优化，提高了产率。
2.合成外琳化合物的光谱性能分析
对所合成叶琳化合物的紫外吸收光谱和荧光光谱进行了分析，对光谱差异予以
了合理解释。
3.叶琳搀杂8一轻基哇琳铝作为发光层的红光器件
为了考察不同叶琳的电致发光性能，进行了器件的制备，器件的结构为nD月于D
/Al q:dopan口Mg:Ag，不同器件的起亮电压均为7V左右，在所制备的器件中，钻叶
琳不发光;TppHZ，T卜C护p玩，乃月刁iMeoppHZ，介.OH，PHZ所对应器件的最大亮
度分别为42，17，17，s.sa刀mZ。
4.外琳液相搀杂8一轻基哇嗽铝对红光器件的仿真模拟
为了进行叶琳液相搀杂8.轻基哇琳铝对红光器件的仿真模拟，探讨叶琳与8一轻
基哇琳铝液相搀杂时的相互作用，测试了不同种类、不同搀杂质盘分数的叶琳与8-
经基喳琳铝在溶液中的光谱行为。研究表明，随着搀杂质量分数的增加，叶琳的荧
光强度增加，冬经基哇琳铝的荧光强度下降。这是由于冬轻基哇琳铝到外琳之间的
能量迁移，导致了哇琳铝荧光的碎灭，不同外琳碎灭程度不同，是因为主体与客体
之间能量迁移效率不同引起的。采用叶琳与8刁径基哇琳铝相对荧光强度比随外琳搀
杂质量分数变化的曲线来描述主客体分子相互作用的强弱，用曲线斜率的大小进行
器件性能预测，从而实现红光染料的化学筛选。
In order to study the synthetic methods and optoelectronic properties of porphyrins, three types of target molecules were designed and synthesized. i.e., meso-substituted porphyrins, β - pyrrolic substituted porphyrins , and both meso- and β -pyrrolic substituted porphyrins; we investigated the spectral properties of all the synthesized porphyrins; we also investigated the luminance of the red organic electroluminescence devices which constructed by using porphyrins as dopant, that was doped at different concentrations(1.5, 2, 2.7, 5 wt%) within a Alq3 host layer; a new chemical selection method for red dyes was obtained by imitation the devices with porphyrins doped into Alqs in chloroform.The main contents are as follows: 1. porphyrins' synthesis
20 porphyrins,i.e.,2,7,12,17-tetramethyl-3,8,13,18-tetraeth ylporphyrin(TMTE,l), 2,7,12,17-tetramethyl-3,8,13,18-tetraethylporphyrin Zinc(II)(TMTEZn,2), Octaethylporphyrin(OEP,3), Octaethylporphyrin Zinc (OEPZn,4), meso-5,10,15,2,0-tetraphenylporphyrin(TPPH2,5), meso-5,10, 15,20-tetraphenylporphyrin Cobalt(II)(TPPCo,6), rneso-5,10,15,20-tetra-(p-hydroxylphenyl)porphyrin(Tp-OHPPH2,7), meso-5,10,15,20-tetra(p-chlorophenyl)porphyrin(Tp-C!PPH2,8), meso-5,10,15,20-tetra(p-methyl -oxylphenyl)porphyrin(Tp-OCH3PPH2,9), meso-5,10,15,20-tetra(3,4-dime thyloxylphenyl)porphyrin(T374-OCH3PPH2,10), meso-5,10,15,20-tetra(p-aminophenyl)porphyrin(TAPPH2,11), meso-5,10,15,20-tetraStyreneporph -yrin(TStPPH2,12), meso-5,10,15,20-tetraBiphenylporphyrin(TBPPH2,13), meso-5,10,15,20-tetra[p~(p-hydroxylbenzeneazo)phenyl]porphyrin [Tp-(p-OHBazo)PPH2,14], meso-5,10,15,20-tetra(p-Hydroxyl-o-Met -hylbenzeneazophenyl)porphyrin[Tp-(p-OH-o-CH3Bazo)PPH2,15], meso-5,10,15,20-tetra(p-Hydroxyl-m-Benzeneazo)phenylporphyrin(Tp-OH-m-
BazoPPH2,16), meso-5,10,15,20-tetra(o-Hydroxyl-m-Benezeneazo)phen-ylporphyrin(To-OH-m-BazoPPH2,17), meso-5,10,15,20-tetra( P -Hydroxyl-naphtolazophenyl)porphyrin[Tp-( 3 -OHNazo)PPH2,18], 2,3,7,8,12,13, 17,18-Octamethyl-5,l 5-di(m-Bromophenyl)-10,20-diphenylporphyrin
[(OM-B-m- BrP-BP)PH2,19], Porphyrin dimmer(DiPPH2,20) have been designed and synthesized. And eight substituted aromatic aldehyde have als -o been synthesized, they are p-phenylbenzaldehyde(21), p-aminobenzalde-hyde(22), (o-Hydroxyl-m-phenylazo)benzaldehyde(23), (p-Hydroxyl-m-ph enylazo)benzaldehyde(24), 4-(p-hydroxylbenzeneazo)benzaldehyde(25), 4-(o-Methyl-p-Hydroxylbenzeneazo)benzaldehyde(26), 4-( 3 -hydroxylnaphto -lazo)benzaldehyde(27), 4,4'-di(o-Hydroxyl-m-formoylbenzeneazo)bipheny -1(28). The compounds, with black label, are new or the synthetic methods are never reported before. All these compounds were characterized by 'HNMR, MS, UV-Vis and IR. Contents of this parts can be sorted as follow: (1) Study on the synthetic methods of porphyrins
After modification of Adler's reaction equipment,i.e.,adding a equipment which adsorbing water, bring the equilibrium to right, yields of porphyrins are improved, condensation of p-aminobenzaldehyde and pyrrole in propanoic acid directly, yield of porphyrin is 25%. Which is nine percent higher than reported (16%) before; Adding template to acetic acid, nitrogen purged, condensation of cassia aldehyde with pyrrole directly, then demetalled, tetrastyreneporphyrin (TStPPH2,12) was obtained in good yield, this kind of porphyrin is never reported before, it's a new synthetic method for porphyrins alike; adopting acetic acid as solvent and template added as well, condensation dipyrrole methane with benzaldehyde under dark and room temperature with stirring, porphyrin[(OM-Bm.BrP-BP)PH2,19]was obtained, this method can be used to synthesize this kind of porphyrin; a series of azoporphyrin were synthesized by condensing azoaldehyde and pyrrole in acetic acid, acetic acid is an ideal medium for azoporphyrins' synthesis; coupling of 5-hydroxylphenyl-10,15,20-trisphenylporphyrin with biphenylenebisazo salt at base solution, porphyrin dimer(DiPPH2,20) was obtained, which expanding the area of coupling reaction between diazo salt
and phenols.
(2) Study on the syn
1．三种类型卟啉的合成研究
设计并合成了20种卟啉化合物，即：四甲基四乙基卟啉(TMTE，1)，四甲基四乙基锌卟啉(TMTEZn，2)，八乙基卟啉(OEP，3)，八乙基锌卟啉(OEPZn，4)，四苯基卟啉(TPPH_2，5)，四苯基钴卟啉(TPPCo，6)，四对羟基苯基卟啉(Tp-OHPPH_2，7)，四对氯苯基卟啉(Tp-ClPPH_2，8)，四对甲氧基苯基卟啉(Tp-MeOPPH_2，9)，四(3，4-二甲氧基苯基)卟啉(T_(3,4)-diMeOPPH_2，10)，四对氨基苯基卟啉(TAPPH_2，11)，四苯乙烯基卟啉(TStPPH_2，12)，四联苯基卟啉(TBPPH_2，13)，四[对(对羟基苯偶氮基)]苯基卟啉[Tp-(p-OHBazo)PPH_2，14]，四[对(对羟基邻甲基苯偶氮基)]苯基卟啉[Tp-(p-OH-o-CH_3Bazo)PPH_2，15]，四(对羟基间苯偶氮基)苯基卟啉(Tp-OH-m-BazoPPH_2，16)，四(邻羟基间苯偶氮基)苯基卟啉(To-OH-m-BazoPPH_2，17)，四[对(β羟基萘偶氮基)]苯基卟啉[Tp-(β-OHNazo)PPH_2，18]，八甲基二间溴代苯基二苯基卟啉[(OM-B-m-BrP-BP)PH_2，19]，偶氮二聚卟啉(DiPPH_2，20)。本文共合成了8种取代芳醛：联苯甲醛(21)，对氨基苯甲醛(22)，邻羟基对苯偶氮基苯甲醛(23)，对羟基间苯偶氮基苯甲醛(24)，4-(对羟基苯偶氮基)苯甲醛(25)，4-(邻甲基对羟基苯偶氮基)苯甲醛(26)，4-(β羟基萘偶氮基)苯甲醛(27)，4,4'-二(邻羟基间甲酰基苯偶氮基)联苯(28)。黑体化合物(12，15，16，17，19，20，24，25，26，27，28)为新化合物；(13，14，18)是采用新方法合成的化合物。这些化合物的结构通过了HNMR，MS，UV-Vis，Elemental analysis及IR表征，本部分主要内容如下：
(1)卟啉合成方法的研究
本文通过对Adler法合成装置的改进，即加一吸水装置，使反应平衡右移，以对氨基苯甲醛与吡咯在丙酸中直接缩合合成卟啉(11)，产率提高了9％；反应体系中
在加入模板剂的同时通入NZ，桂皮醛与毗咯在醋酸中缩合合成了四苯乙烯基锌叶
琳，用盐酸脱锌得四苯乙烯基叶啦口段PpH全，12)，对于烯基醛与毗咯直接缩合合
成叶琳的方法未见相关文献报道，是一种新的合成方法;采用醋酸为溶剂，在模板
剂作用下，避光避热，常温搅拌，后期回流的方法合成了[( OM.卜m七fP一巧PHZ，
1外这对于合成光热敏感的化合物具有很好的借鉴意义;采用醋酸为溶剂，用偶氮
醛与毗咯一步缩合合成了系列偶氮叶琳，醋酸是一种合成对称偶氮n卜琳的理想介质;
采用联苯二胺重氮盐与单经基p卜琳在碱性条件下直接偶合，合成了偶氮二聚叶琳，
拓宽了重氮盐与酚的作用范围。
(2)中间体合成研究
利用重氮偶合反应合成了系列芳香偶氮醛，采用抓甲基法成功制备了联苯甲醛，
利用Khorr反应合成了毗咯衍生物，对中间体的合成进行了优化，提高了产率。
2.合成外琳化合物的光谱性能分析
对所合成叶琳化合物的紫外吸收光谱和荧光光谱进行了分析，对光谱差异予以
了合理解释。
3.叶琳搀杂8一轻基哇琳铝作为发光层的红光器件
为了考察不同叶琳的电致发光性能，进行了器件的制备，器件的结构为nD月于D
/Al q:dopan口Mg:Ag，不同器件的起亮电压均为7V左右，在所制备的器件中，钻叶
琳不发光;TppHZ，T卜C护p玩，乃月刁iMeoppHZ，介.OH，PHZ所对应器件的最大亮
度分别为42，17，17，s.sa刀mZ。
4.外琳液相搀杂8一轻基哇嗽铝对红光器件的仿真模拟
为了进行叶琳液相搀杂8.轻基哇琳铝对红光器件的仿真模拟，探讨叶琳与8一轻
基哇琳铝液相搀杂时的相互作用，测试了不同种类、不同搀杂质盘分数的叶琳与8-
经基喳琳铝在溶液中的光谱行为。研究表明，随着搀杂质量分数的增加，叶琳的荧
光强度增加，冬经基哇琳铝的荧光强度下降。这是由于冬轻基哇琳铝到外琳之间的
能量迁移，导致了哇琳铝荧光的碎灭，不同外琳碎灭程度不同，是因为主体与客体
之间能量迁移效率不同引起的。采用叶琳与8刁径基哇琳铝相对荧光强度比随外琳搀
杂质量分数变化的曲线来描述主客体分子相互作用的强弱，用曲线斜率的大小进行
器件性能预测，从而实现红光染料的化学筛选。
In order to study the synthetic methods and optoelectronic properties of porphyrins, three types of target molecules were designed and synthesized. i.e., meso-substituted porphyrins, β - pyrrolic substituted porphyrins , and both meso- and β -pyrrolic substituted porphyrins; we investigated the spectral properties of all the synthesized porphyrins; we also investigated the luminance of the red organic electroluminescence devices which constructed by using porphyrins as dopant, that was doped at different concentrations(1.5, 2, 2.7, 5 wt%) within a Alq3 host layer; a new chemical selection method for red dyes was obtained by imitation the devices with porphyrins doped into Alqs in chloroform.The main contents are as follows: 1. porphyrins' synthesis
20 porphyrins,i.e.,2,7,12,17-tetramethyl-3,8,13,18-tetraeth ylporphyrin(TMTE,l), 2,7,12,17-tetramethyl-3,8,13,18-tetraethylporphyrin Zinc(II)(TMTEZn,2), Octaethylporphyrin(OEP,3), Octaethylporphyrin Zinc (OEPZn,4), meso-5,10,15,2,0-tetraphenylporphyrin(TPPH2,5), meso-5,10, 15,20-tetraphenylporphyrin Cobalt(II)(TPPCo,6), rneso-5,10,15,20-tetra-(p-hydroxylphenyl)porphyrin(Tp-OHPPH2,7), meso-5,10,15,20-tetra(p-chlorophenyl)porphyrin(Tp-C!PPH2,8), meso-5,10,15,20-tetra(p-methyl -oxylphenyl)porphyrin(Tp-OCH3PPH2,9), meso-5,10,15,20-tetra(3,4-dime thyloxylphenyl)porphyrin(T374-OCH3PPH2,10), meso-5,10,15,20-tetra(p-aminophenyl)porphyrin(TAPPH2,11), meso-5,10,15,20-tetraStyreneporph -yrin(TStPPH2,12), meso-5,10,15,20-tetraBiphenylporphyrin(TBPPH2,13), meso-5,10,15,20-tetra[p~(p-hydroxylbenzeneazo)phenyl]porphyrin [Tp-(p-OHBazo)PPH2,14], meso-5,10,15,20-tetra(p-Hydroxyl-o-Met -hylbenzeneazophenyl)porphyrin[Tp-(p-OH-o-CH3Bazo)PPH2,15], meso-5,10,15,20-tetra(p-Hydroxyl-m-Benzeneazo)phenylporphyrin(Tp-OH-m-
BazoPPH2,16), meso-5,10,15,20-tetra(o-Hydroxyl-m-Benezeneazo)phen-ylporphyrin(To-OH-m-BazoPPH2,17), meso-5,10,15,20-tetra( P -Hydroxyl-naphtolazophenyl)porphyrin[Tp-( 3 -OHNazo)PPH2,18], 2,3,7,8,12,13, 17,18-Octamethyl-5,l 5-di(m-Bromophenyl)-10,20-diphenylporphyrin
[(OM-B-m- BrP-BP)PH2,19], Porphyrin dimmer(DiPPH2,20) have been designed and synthesized. And eight substituted aromatic aldehyde have als -o been synthesized, they are p-phenylbenzaldehyde(21), p-aminobenzalde-hyde(22), (o-Hydroxyl-m-phenylazo)benzaldehyde(23), (p-Hydroxyl-m-ph enylazo)benzaldehyde(24), 4-(p-hydroxylbenzeneazo)benzaldehyde(25), 4-(o-Methyl-p-Hydroxylbenzeneazo)benzaldehyde(26), 4-( 3 -hydroxylnaphto -lazo)benzaldehyde(27), 4,4'-di(o-Hydroxyl-m-formoylbenzeneazo)bipheny -1(28). The compounds, with black label, are new or the synthetic methods are never reported before. All these compounds were characterized by 'HNMR, MS, UV-Vis and IR. Contents of this parts can be sorted as follow: (1) Study on the synthetic methods of porphyrins
After modification of Adler's reaction equipment,i.e.,adding a equipment which adsorbing water, bring the equilibrium to right, yields of porphyrins are improved, condensation of p-aminobenzaldehyde and pyrrole in propanoic acid directly, yield of porphyrin is 25%. Which is nine percent higher than reported (16%) before; Adding template to acetic acid, nitrogen purged, condensation of cassia aldehyde with pyrrole directly, then demetalled, tetrastyreneporphyrin (TStPPH2,12) was obtained in good yield, this kind of porphyrin is never reported before, it's a new synthetic method for porphyrins alike; adopting acetic acid as solvent and template added as well, condensation dipyrrole methane with benzaldehyde under dark and room temperature with stirring, porphyrin[(OM-Bm.BrP-BP)PH2,19]was obtained, this method can be used to synthesize this kind of porphyrin; a series of azoporphyrin were synthesized by condensing azoaldehyde and pyrrole in acetic acid, acetic acid is an ideal medium for azoporphyrins' synthesis; coupling of 5-hydroxylphenyl-10,15,20-trisphenylporphyrin with biphenylenebisazo salt at base solution, porphyrin dimer(DiPPH2,20) was obtained, which expanding the area of coupling reaction between diazo salt
and phenols.
(2) Study on the syn
引文
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