CN106632500B - 基于2-(4-(二米基硼)苯基)吡啶配体的铱(iii)配合物及其制备方法和应用 - Google Patents

基于2-(4-(二米基硼)苯基)吡啶配体的铱(iii)配合物及其制备方法和应用 Download PDF

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CN106632500B
CN106632500B CN201611149995.3A CN201611149995A CN106632500B CN 106632500 B CN106632500 B CN 106632500B CN 201611149995 A CN201611149995 A CN 201611149995A CN 106632500 B CN106632500 B CN 106632500B
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phenyl
dimesitylboryl
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杨凌霞
于振涛
祝梅
邹志刚
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Yangzhou Wanrun Photoelectric Technology Co ltd
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Nanjing University
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Abstract

本发明涉及一种基于2‑(4‑(二米基硼)苯基)吡啶配体的铱(III)配合物,其化学通式为[Ir(p‑B‑ppy)2(N^N)](PF6),其中p‑B‑ppy为2‑(4‑(二米基硼)苯基)吡啶,N^N为联吡啶[3,2‑a:2',3'‑c]吩嗪或联吡啶[3,2‑f:2',3'‑h]喹喔啉或1,10‑菲啰啉。制备方法:将铱(III)配合物中间体和N^N加入到甲醇和二氯甲烷的混合溶液中,在N2氛围中于80℃回流20‑30h,再加入六氟磷酸铵,继续回流,反应结束后,将产物提纯即得。本发明的铱(III)配合物具有优异的光化学性能,发光效果好,寿命长,可应用于光催化分解水制备氢气,并且出氢效率高。

Description

基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物及其 制备方法和应用
技术领域
本发明涉及一种基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物,属于光催化剂技术领域。
背景技术
化石能源的消耗不仅造成能源短缺,也带来了严峻的环境问题。开发环境友好、成本低廉、来源丰富的可再生清洁能源是社会发展面临的巨大挑战。利用自然界丰富的太阳能进行人工模拟光合作用是人类一直不断努力追求的目标。基于光敏剂、催化剂和牺牲剂的三组分光致析氢体系是科学家研究的热点。理想的光敏剂应当具有良好的可见光吸收,适中的氧化还原电位,寿命较长的激发态,且能循环利用。
现有技术中,比较常用的光敏剂为钌类光敏剂,如[Ru(dmphen)3](PF6)2,其中dmphen为4,7-二甲基-1,10-菲啰啉,但其存在出氢效率低、稳定性不佳、激发态难以被催化剂淬灭、摩尔消光系数低等缺点,在已有的体系中,光致析氢TON数值仅仅只有92(TON代表光敏剂的催化活性,其数值越高,代表光敏剂的催化活性越好)。
发明内容
本发明的目的在于解决现有技术的不足,提供一种基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物,其具有优异的光化学性能,发光效果好,寿命长,可作为光催化分解水制备氢气的光敏剂,并且出氢效率高,稳定性佳。
技术方案
一种基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物,其化学通式为[Ir(p-B-ppy)2(N^N)](PF6),其中p-B-ppy为2-(4-(二米基硼)苯基)吡啶,N^N为联吡啶[3,2-a:2',3'-c]吩嗪、联吡啶[3,2-f:2',3'-h]喹喔啉或1,10-菲啰啉中的任意一种。
作为优选,所述N^N为联吡啶[3,2-a:2',3'-c]吩嗪,出氢效果更好。
所述基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物的结构式有以下三种:
所述基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物的制备方法,包括如下步骤:
(1)将铱(III)配合物中间体(Ir(p-B-ppy)2Cl2)和N^N配体加入到甲醇和二氯甲烷的混合溶剂中,混合均匀后在N2氛围中于80℃下回流20-30h,得到反应液;
(2)将六氟磷酸铵加入步骤(1)的反应液中,继续回流2-5h,反应结束后,将反应得到的产物提纯,即得。
所述铱(III)配合物中间体、N^N配体和六氟磷酸铵的摩尔比为1:2.5:10。
步骤(1)中,所述甲醇和二氯甲烷的混合溶剂中,甲醇和二氯甲烷的体积比为1:1。
步骤(1)中,所述铱(III)配合物中间体的制备方法:将配体2-(4-(二米基硼)苯基)吡啶、氯化铱水合物加入2-乙氧基乙醇的水溶液中,在N2氛围中于140℃下回流24h,反应停止后,冷却,过滤,再分别用水、乙醇、丙酮洗涤,最后烘干,得到橙红色粉末即为铱(III)配合物中间体;所述2-(4-(二米基硼)苯基)吡啶和三氯化铱的摩尔比为3:1,2-乙氧基乙醇的水溶液中,2-乙氧基乙醇与水的体积比为3:1。
步骤(2)中,所述提纯方法为:将反应得到的产物旋干,然后在硅胶柱中以体积比为5:1的二氯甲烷和乙醇为洗脱剂进行色谱分离,最后再经过重结晶。
上述基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物在光催化分解水制氢中的应用,本发明的铱(III)配合物可作为光敏剂参与光催化分解水制氢,现有技术中已经报道了某些光敏剂(例如钌类光敏剂),实现可见光催化分解水制备氢气的方法,本发明可以采用这些已有的光催化分解水的方法。例如可以是,将基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物、四氯铂酸钾(K2PtCl4)、三乙醇胺(TEOA),加入100mL乙腈/水(v/v=4:1)混合溶液中,用盐酸调节pH至7.0,在可见光照射下进行光催化分解水制氢。所述基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物为光敏剂,TEOA为牺牲剂,四氯铂酸钾(K2PtCl4)作为催化剂。TEOA、四氯铂酸钾(K2PtCl4)的用量均为现有技术。
有益效果:本发明的铱(III)配合物适和用作光催化分解水制备氢气的光敏剂,其具有优异的光化学性能,发光效果好,寿命长,用于光催化分解水制备氢气时,出氢效率高,稳定性佳。
附图说明
图1为实施例1的基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物的H谱图;
图2为实施例2的基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物的H谱图;
图3为实施例3的基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物的H谱图;
图4为实施例1-3的基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物在CH2Cl2溶液中的发射光谱图;
图5为实施例1-3的基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物在CH2Cl2溶液中的激发态寿命图;
图6为实施例1-3的基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物在[Co(bpy)3]Cl2作为淬灭剂时的Stern-Volmer曲线;
图7为实施例1-3的基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物用于光催化分解水制氢的氢气产出图。
具体实施方式
下面结合附图和实施例对本发明作进一步说明。
实施例1
制备铱(III)配合物中间体:将配体2-(4-(二米基硼)苯基)吡啶853mg、氯化铱水合物223mg加入到60mL 2-乙氧基乙醇的水溶液(2-乙氧基乙醇:水=3:1)中,在N2氛围中于140℃下回流24h。反应停止,冷却,过滤,再分别用10mL水、10mL乙醇、10mL丙酮洗涤、烘干,得到橙红色粉末。
将铱(III)配合物中间体418mg与联吡啶[3,2-a:2',3'-c]吩嗪(2.5eq)、无水碳酸钠(10eq)加入40mL甲醇和二氯甲烷混合溶液(CH3OH:CH2Cl2=1:1)中,在N2氛围中于80℃下回流24h;再将六氟磷酸铵(10eq)加入上述反应液中,继续回流大约3h,反应结束后,将溶剂旋干后在硅胶柱中以体积比为5:1的二氯甲烷和乙醇为洗脱剂进行色谱分离,经过重结晶过程得到铱(III)配合物。产量430mg(75%)。
将铱(III)配合物进行核磁共振(H谱图见图1),测得:1H NMR(300MHz,CD3CN)δ9.75(dd,J=8.3,1.4Hz,2H),8.46(ddd,J=6.7,5.7,2.1Hz,4H),8.18–8.11(m,2H),8.00(dd,J=8.3,5.2Hz,2H),7.83(dd,J=14.8,7.9Hz,4H),7.56–7.47(m,2H),7.40(d,J=5.2Hz,2H),7.12(dd,J=7.8,1.1Hz,2H),6.77(s,8H),6.65–6.57(m,2H),6.27(d,J=0.7Hz,2H),2.32(s,12H),1.85(d,J=9.5Hz,24H).ESI-MS:m/z=1279.67[M+].
实施例2
铱(III)配合物中间体的制备同实施例1。
将Ir(III)配合物的中间体300mg与联吡啶[3,2-f:2',3'-h]喹喔啉(2.5eq)、无水碳酸钠(10eq)加入40mL甲醇和二氯甲烷混合溶液(CH3OH:CH2Cl2=1:1)中,在N2氛围中于80℃下回流24h;再将六氟磷酸铵(10eq)加入上述反应液中,继续回流大约3h,反应结束后,将溶剂旋干后在硅胶柱中以体积比为5:1的二氯甲烷和乙醇为洗脱剂进行色谱分离,经过重结晶过程得到铱(III)配合物。产量250mg(62%)。
将铱(III)配合物进行核磁共振(H谱图见图2),测得:1H NMR(300MHz,CD3CN)δ9.65(dd,J=8.3,1.3Hz,2H),9.23(s,2H),8.45(dt,J=12.9,6.5Hz,2H),8.00(dd,J=8.3,5.1Hz,2H),7.82(dd,J=13.8,7.8Hz,4H),7.55–7.44(m,2H),7.32(d,J=5.4Hz,2H),7.12(dd,J=7.7,0.9Hz,2H),6.76(s,8H),6.62–6.53(m,2H),6.26(s,2H),2.30(d,J=11.1Hz,12H),1.94–1.66(m,24H).ESI-MS:m/z=1229.58[M+].
实施例3
铱(III)配合物中间体的制备同实施例1。
将铱(III)配合物的中间体410mg与1,10-菲啰啉(2.5eq)、无水碳酸钠(10eq)加入40mL甲醇和二氯甲烷混合溶液(CH3OH:CH2Cl2=1:1)中,在N2氛围中于80℃下回流24h;再将六氟磷酸铵(10eq)加入上述反应液中,继续回流大约3h,反应结束后,将溶剂旋干后在硅胶柱中以体积比为5:1的二氯甲烷和乙醇为洗脱剂进行色谱分离,经过重结晶过程得到铱(III)配合物。产量380mg(71%)。
将铱(III)配合物进行核磁共振(H谱图见图3),测得:1H NMR(300MHz,CD3CN)δ8.69(dd,J=8.3,1.3Hz,2H),8.35(dd,J=5.0,1.3Hz,2H),8.24(s,2H),7.91–7.73(m,6H),7.54–7.43(m,2H),7.21(d,J=5.2Hz,2H),7.10(dd,J=7.8,1.0Hz,2H),6.75(s,8H),6.61–6.49(m,2H),6.27(s,2H),2.30(d,J=5.1Hz,12H),1.83(d,J=10.0Hz,24H).ESI-MS:m/z=1177.67[M+].
性能测试
1、将实施例1-3制备的基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物分别溶解于CH2Cl2,配制成浓度为10-5M溶液,测其发射光谱与发光寿命(发射光谱图见图4,激发态寿命图见图5),然后分别加入不同量淬灭剂[Co(bpy)3]Cl2,测其发射光谱,溶液发光强度随着淬灭剂加入量的增多而降低,溶液发光强度遵循Stern-Volmer方程,Stern-Volmer曲线见图6。
由图4可以看出,实施例1-3的铱(III)配合物的发射峰分别为632nm、605nm、582nm,这说明实施例1-3的铱(III)配合物的发光效果好,由图5可以得出,实施例1-3的铱(III)配合物的发光寿命分别为0.67us、0.63us、1.42us,发光寿命长。由图6的Stern-Volmer曲线计算得出淬灭剂对实施例1-3的铱(III)配合物激发态的淬灭常数Kq分别为1.29×1010M-1S-1、5.08×109M-1S-1、2.74×109M-1S-1,这说明本发明实施例制备的铱(III)配合物具有激发态易淬灭的优势。
2、将实施例1-3制备的基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物分别用于光催化分解水制备氢气,测试方法为:将40μmol基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物加入到含有0.1mM四氯铂酸钾,0.2M三乙醇胺的中性乙腈/水(v/v=4:1)混合溶液中(100mL),将反应器中的空气抽空后,在300W氙灯下照射(λ>420nm),反应生成的氢气经气相色谱定量分析,测试结果见图7。
由图7可以看出,实施例1-3的铱(III)配合物所在体系在光照20h后生成氢气的量分别为490μmol、124μmol、192μmol,计算三种配合产氢的TON数值分别为490、124、192,可以看出实施例1的铱(III)配合物的产氢量最高。现有技术的钌类催化剂例如[Ru(dmphen)3](PF6)2,其中dmphen为4,7-二甲基-1,10-菲啰啉,其光致析氢TON数值仅仅只有92,与之相比,本发明的铱(III)配合物产氢效率更高。

Claims (7)

1.一种基于2-[4-(二米基硼)苯基]吡啶配体的铱(III)配合物,其特征在于,其化学通式为[Ir(p-B-ppy)2(N^N)](PF6),其中p-B-ppy为2-[4-(二米基硼)苯基]吡啶,N^N为联吡啶[3,2-a:2',3'-c]吩嗪、联吡啶[3,2-f:2',3'-h]喹喔啉或1,10-菲啰啉中的任意一种;
所述基于2-(4-(二米基硼)苯基)吡啶配体的铱(III)配合物的结构式为以下三种之一:
2.如权利要求1所述的基于2-[4-(二米基硼)苯基]吡啶配体的铱(III)配合物,其特征在于,所述N^N为联吡啶[3,2-a:2',3'-c]吩嗪。
3.权利要求1或2所述基于2-[4-(二米基硼)苯基]吡啶配体的铱(III)配合物的制备方法,其特征在于,包括如下步骤:
(1)将铱(III)配合物中间体Ir(p-B-ppy)2Cl2和N^N配体加入到甲醇和二氯甲烷的混合溶剂中,混合均匀后在N2氛围中于80℃下回流20-30h,得到反应液;
(2)将六氟磷酸铵加入步骤(1)的反应液中,继续回流2-5h,反应结束后,将反应得到的产物提纯,即得;
所述铱(III)配合物中间体、N^N配体和六氟磷酸铵的摩尔比为1:2.5:10。
4.如权利要求3所述的制备方法,其特征在于,步骤(1)中,所述甲醇和二氯甲烷的混合溶剂中,甲醇和二氯甲烷的体积比为1:1。
5.如权利要求3所述的制备方法,其特征在于,步骤(1)中,所述铱(III)配合物中间体的制备方法为:将配体2-[4-(二米基硼)苯基]吡啶、氯化铱水合物加入2-乙氧基乙醇的水溶液中,在N2氛围中于140℃下回流24h,反应停止后,冷却,过滤,再分别用水、乙醇、丙酮洗涤,最后烘干,得到橙红色粉末即为铱(III)配合物中间体;所述2-[4-(二米基硼)苯基]吡啶和三氯化铱的摩尔比为3:1,所述2-乙氧基乙醇的水溶液中,2-乙氧基乙醇与水的体积比为3:1。
6.如权利要求3或4或5所述的制备方法,其特征在于,步骤(2)中,所述提纯方法为:将反应得到的产物旋干,然后在硅胶柱中以体积比为5:1的二氯甲烷和乙醇为洗脱剂进行色谱分离,最后再经过重结晶。
7.权利要求1或2所述基于2-[4-(二米基硼)苯基]吡啶配体的铱(III)配合物在光催化分解水制氢中的应用。
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