新型螺吡喃衍生物: 离子传感和分子水平的信息处理

doi:10.3866/PKU.WHXB201205155

物理化学学报 >> 2012, Vol. 28 >> Issue (10): 2471-2479.doi: 10.3866/PKU.WHXB201205155

新型螺吡喃衍生物: 离子传感和分子水平的信息处理

李颖若¹, 张洪涛², 齐传民¹, 郭雪峰^2,3

1. 北京师范大学化学学院, 放射性药物教育部重点实验室, 北京100875;
2. 北京大学化学与分子工程学院, 北京分子科学国家实验室, 分子动态与稳态结构国家重点实验室, 北京 100871;
3. 北京大学工学院先进材料与纳米技术系, 北京 100871

收稿日期:2012-03-31 修回日期:2012-05-14 发布日期:2012-09-26
通讯作者: 齐传民, 郭雪峰 E-mail:guoxf@pku.edu.cn; qichuanmin@bnu.edu.cn
基金资助:
国家重点基础研究发展规划项目(973) (2009CB623703, 2012CB921404), 国家自然科学基金(20833001, 51121091, 2112016, 21071022)及全国高等学校优秀博士论文作者专项基金(2007B21)资助

New Spiropyran Derivatives: Ion Sensing and Information Processing at the Molecular Level

LI Ying-Ruo¹, ZHANG Hong-Tao², QI Chuan-Min¹, GUO Xue-Feng^2,3

1. Key Laboratory of Radiopharmaceuticals, Department of Chemistry, Beijing Normal University, Beijing 100875, P. R. China;
2. Beijing National Laboratory for Molecular Sciences, State Key Laboratory for Structural Chemistry of Unstable and Stable Species, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. China;
3. Department of Advanced Materials and Nanotechnology, College of Engineering, Peking University, Beijing 100871, P. R. China

Received:2012-03-31 Revised:2012-05-14 Published:2012-09-26
Contact: QI Chuan-Min, GUO Xue-Feng E-mail:guoxf@pku.edu.cn; qichuanmin@bnu.edu.cn
Supported by:
The project was supported by the National Key Basic Research Program of China (973) (2009CB623703, 2012CB921404), National Natural Science Foundation of China (20833001, 51121091, 2112016, 21071022), and Foundation for the Author of National Excellent Doctoral Dissertation of Higher Education, China (2007B21).

摘要/Abstract

摘要：

为实现金属离子检测和分子水平的信息处理, 合成了一类新型的含有功能配位基团的螺吡喃衍生物(SP1-SP4). 研究发现: 在没有UV光照的条件下, 金属离子可以促进螺吡喃(SP2和SP4)开环并形成稳定可逆的络合物(MC-Mⁿ⁺). 紫外-可见吸收光谱研究表明, 在UV光照前加入不同的金属离子会引起SP2 和SP4 的光学性质的特征变化, 因此提供了一种简易的通过裸眼就能辨别金属离子的比色方法. 荧光光谱研究表明, 这类化合物能够高灵敏高选择性地检测锌离子. 此外, 基于吸收光谱和荧光光谱的变化, 这类螺吡喃衍生物可以用于构建组合的逻辑门, 执行分子水平的信息处理, 从而展现了其在化学或环境传感和未来的分子计算机领域的潜在应用前景.

关键词: 螺吡喃, 化学传感, 逻辑门, 紫外-可见吸收光谱, 荧光光谱

Abstract:

We have designed and synthesized a new class of spiropyran derivatives (SP1-SP4) with functional chelating groups, such as pyridine or quinoline moieties and a methoxy group (―OMe), for use in metal ion sensing and information processing at the molecular level. It is notable that metal ions can favor coordination with chelating groups and facilitate the photoisomerization of spiropyran molecules from the closed form to the open merocyanine form without UV irradiation, thus leading to significant changes in their chemical and physical properties. UV-Vis absorption studies indicated that SP2 and SP4 exhibited metal ion-dependent reversible binding affinities that result in different hypsochromic shifts for the MC-Mⁿ⁺ complexes. These changes in color can be recognized by eye, thus offering an easy colorimetric method for metal ion detection. Further emission studies distinguished them as promising candidates for Zn2+ detection with good sensitivity and selectivity. Moreover, on the basis of their absorption and fluorescence spectra, several combinational logic gates were constructed for information processing at the molecular level. These results demonstrate that spiropyran derivatives with desired functionalities show great potential not only for chemical or environmental sensors, but also for future molecular computing.

Key words: Spiropyran, Chemical sensor, Logic gate, UV-Vis absorption spectrum, Fluorescence spectrum

点击下载补充材料PDF格式文件

李颖若, 张洪涛, 齐传民, 郭雪峰. 新型螺吡喃衍生物: 离子传感和分子水平的信息处理[J]. 物理化学学报, 2012, 28(10), 2471-2479. doi: 10.3866/PKU.WHXB201205155

LI Ying-Ruo, ZHANG Hong-Tao, QI Chuan-Min, GUO Xue-Feng. New Spiropyran Derivatives: Ion Sensing and Information Processing at the Molecular Level[J]. Acta Phys. -Chim. Sin. 2012, 28(10), 2471-2479. doi: 10.3866/PKU.WHXB201205155

链接本文: https://www.whxb.pku.edu.cn/CN/10.3866/PKU.WHXB201205155

https://www.whxb.pku.edu.cn/CN/Y2012/V28/I10/2471

参考文献

(1) Irie, M. Chem. Rev. 2000, 100, 1685. doi: 10.1021/cr980069d
(2) Irie, M.; Fukaminato, T.; Sasaki, T.; Tamai, N.; Kawai, T. Nature2002, 420, 759. doi: 10.1038/420759a
(3) de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley,A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515. doi: 10.1021/cr960386p
(4) Kocer, A.;Walko, M.; Meijberg,W.; Feringa, B. L. Science2005, 309, 755. doi: 10.1126/science.1114760
(5) Berkovic, G.; Krongauz, V.;Weiss, V. Chem. Rev. 2000, 100,1741. doi: 10.1021/cr9800715
(6) Guo, X.; Zhang, D.; Zhu, D. Adv. Mater. 2004, 16, 125. doi: 10.1002/adma.200306102
(7) Kawata, S.; Kawata, Y. Chem. Rev. 2000, 100, 1777. doi: 10.1021/cr980073p
(8) Delaire, J. A.; Nakatani, K. Chem. Rev. 2000, 100, 1817. doi: 10.1021/cr980078m
(9) Tamai, N.; Miyasaka, H. Chem. Rev. 2000, 100, 1875. doi: 10.1021/cr9800816
(10) Guo, X.; Zhang, D.; Yu, G.;Wan, M.; Li, J.; Liu, Y.; Zhu, D.Adv. Mater. 2004, 16, 636. doi: 10.1002/adma.200305792
(11) Shen, Q.;Wang, L.; Liu, S.; Cao, Y.; Gan, L.; Guo, X.;Steigerwald, M. L.; Shuai, Z.; Liu, Z.; Nuckolls, C. Adv. Mater.2010, 22, 3282. doi: 10.1002/adma.201000471
(12) Guo, X.; Huang, L.; O'Brien, S.; Kim, P.; Nuckolls, C. J. Am. Chem. Soc. 2005, 127, 15045. doi: 10.1021/ja054335y
(13) Lee, H. Y.; Diehn, K. K.; Sun, K.; Chen, T.; Raghavan, S. R.J. Am. Chem. Soc. 2011, 133, 8461. doi: 10.1021/ja202412z
(14) Vlassiouk, I.; Park, C. D.; Vail, S. A.; Gust, D.; Smirnov, S.Nano Lett. 2006, 6, 1013. doi: 10.1021/nl060313d
(15) Guo, X.; Zhang, D.; Tao, H.; Zhu, D. Org. Lett. 2004, 6, 2491.doi: 10.1021/ol0494111
(16) Zhang, H.; Guo, X.; Hui, J.; Hu, S.; Xu,W.; Zhu, D. Nano Lett.2011, 11, 4939. doi: 10.1021/nl2028798
(17) Jiang, G.; Song, Y.; Guo, X.; Zhang, D.; Zhu, D. Adv. Mater.2008, 20, 2888. doi: 10.1002/adma.200800666
(18) Shao, N.; Zhang, Y.; Cheung, S.; Yang, R.; Chan,W.; Mo, T.; Li,K.; Liu, F. Anal. Chem. 2005, 77, 7294. doi: 10.1021/ac051010r
(19) Sakamoto, H.; Takagaki, H.; Nakamura, M.; Kimura, K. Anal. Chem. 2005, 77, 1999. doi: 10.1021/ac048642i
(20) Inouye, M.; Akamatsu, K.; Nakazumi, H. J. Am. Chem. Soc.1997, 119, 9160. doi: 10.1021/ja9707668
(21) Shiraishi, Y.; Adachi, K.; Itoh, M.; Hirai, T. Org. Lett. 2009, 11,3482. doi: 10.1021/ol901399a
(22) Takase, M.; Inouye, M. Chem. Commun. 2001, 2432.
(23) Shao, N.; Jin, J. Y.; Cheung, S. M.; Yang, R. H.; Chan,W. H.;Mo, T. Angew. Chem. Int. Edit. 2006, 45, 4944. doi: 10.1002/anie.200600112
(24) Andersson, J.; Li, S.; Lincoln, P.; Andréasson, J. J. Am. Chem. Soc. 2008, 130, 11836. doi: 10.1021/ja801968f
(25) de Silva, A. P.; Gunaratne, H. Q. N.; McCoy, C. P. Nature 1993,364, 42. doi: 10.1038/364042a0
(26) de Silva, A. P.; Gunaratne, H. Q. N.; McCoy, C. P. J. Am. Chem. Soc. 1997, 119, 7891. doi: 10.1021/ja9712229
(27) de Silva, A. P.; McClenaghan, N. D. J. Am. Chem. Soc. 2000,122, 3965. doi: 10.1021/ja994080m
(28) Guo, X.; Zhang, D.; Zhou, Y.; Zhu, D. J. Org. Chem. 2003, 68,5681. doi: 10.1021/jo034243w
(29) Raymo, F. M. Adv. Mater. 2002, 14, 401. doi: 10.1002/1521-4095(20020318)14:6<401::AID-ADMA401>3.0.CO;2-F
(30) Guo, X.; Zhang, D.; Zhang, G.; Zhu, D. J. Phys. Chem. B. 2004,108, 11942. doi: 10.1021/jp047706q
(31) Guo, X.; Zhang, D.;Wang, T.; Zhu, D. Chem. Commun. 2003,914.
(32) Raymo, F. M.; Giordani, S. J. Am. Chem. Soc. 2001, 123, 4651.doi: 10.1021/ja005699n
(33) Hirano, M.; Osakada, K.; Nohira, H.; Miyashita, A. J. Org. Chem. 2001, 67, 533.
(34) Guo, X.; Zhou, Y.; Zhang, D.; Yin, B.; Liu, Z.; Liu, C.; Lu, Z.;Huang, Y.; Zhu, D. J. Org. Chem. 2004, 69, 8924. doi: 10.1021/jo0487799
(35) Shao, N.; Jin, J.;Wang, H.; Zheng, J.; Yang, R.; Chan,W.;Abliz, Z. J. Am. Chem. Soc. 2009, 132, 725.
(36) Natali, M.; Soldi, L.; Giordani, S. Tetrahedron 2010, 66, 7612.doi: 10.1016/j.tet.2010.07.035
(37) Fries, K. H.; Driskell, J. D.; Samanta, S.; Locklin, J. Anal. Chem. 2010, 82, 3306. doi: 10.1021/ac1001004
(38) Paramonov, S. V.; Lokshin, V.; Fedorova, O. A. J. Photochem. Photobiol. C: Photochem. Rev. 2011, 12, 209. doi: 10.1016/j.jphotochemrev.2011.09.001
(39) Poonia, N. S.; Bajaj, A. V. Chem. Rev. 1979, 79, 389. doi: 10.1021/cr60321a002
(40) Abdullah, A.; Roxburgh, C. J.; Sammes, P. G. Dyes and Pigments 2008, 76, 319. doi: 10.1016/j.dyepig.2006.09.002
(41) Ipe, B. I.; Mahima, S.; Thomas, K. G. J. Am. Chem. Soc. 2003,125, 7174. doi: 10.1021/ja0341182
(42) Nolan, E. M.; Lippard, S. J. Accounts Chem. Res. 2008, 42, 193.
(43) Huang, S.; Clark, R. J.; Zhu, L. Org. Lett. 2007, 9, 4999. doi: 10.1021/ol702208y
(44) Kowalczyk, T.; Lin, Z.; Voorhis, T. V. J. Phys. Chem. A 2010,114, 10427.
(45) Winkler, J. D.; Bowen, C. M.; Michelet, V. J. Am. Chem. Soc.1998, 120, 3237. doi: 10.1021/ja974181p
(46) Zhao, J.; Nelson, D. J. J. Inorg. Biochem. 2005, 99, 383. doi: 10.1016/j.jinorgbio.2004.10.005
(47) Torrado, A.;Walkup, G. K.; Imperiali, B. J. Am. Chem. Soc.1998, 120, 609. doi: 10.1021/ja973357k
(48) Saghatelian, A.; Völcker, N. H.; Guckian, K. M.; Lin, V. S. Y.;Ghadiri, M. R. J. Am. Chem. Soc. 2002, 125, 346.
(49) Qu, D. H.; Ji, F. Y.;Wang, Q. C.; Tian, H. Adv. Mater. 2006, 18,2035. doi: 10.1002/adma.200600235
(50) de Sousa, M.; Kluciar, M.; Abad, S.; Miranda, M. A.; de Castro,B.; Pischel, U. Photochem. Photobiol. Sci. 2004, 3, 639. doi: 10.1039/b406415a

[1]	周孟雪, 任宁, 张建军. 2, 4, 6-三甲基苯甲酸与5, 5'-二甲基-2, 2'-联吡啶构筑的系列镧系超分子配合物的晶体结构、热分解机理和性能[J]. 物理化学学报, 2021, 37(10): 2004071 - .
[2]	覃方红, 万婷, 邱江源, 王一惠, 肖碧源, 黄在银. 基于光微热量-荧光光谱联用技术研究光催化热力学和动力学的温度效应[J]. 物理化学学报, 2020, 36(6): 1905087 - .
[3]	曹丹丹, 吕荣, 于安池. 高光学质量氮化碳薄膜的制备和表征[J]. 物理化学学报, 2019, 35(4): 442 -450 .
[4]	武红英, 仲敬荣, 李英秋, 王少飞. 盐酸中Pu(III), Pu(IV), Pu(VI)的制备及紫外-可见吸收光谱[J]. 物理化学学报, 2015, 31(Suppl): 49 -53 .
[5]	库里松·哈衣尔别克,赵淑贤,杨阳,曾涵. 固酶氮掺杂碳纳米复合物基燃料电池性能[J]. 物理化学学报, 2015, 31(9): 1715 -1726 .
[6]	李博轩,郭前进,夏安东. 离子液体[bmim][PF₆]与[moemim][PF₆]结构微不均匀性以及微粘度的光谱探测[J]. 物理化学学报, 2015, 31(8): 1452 -1460 .
[7]	陈晨,逯丹凤,程进,祁志美. 银膜表面等离子体耦合辐射特性的仿真分析[J]. 物理化学学报, 2015, 31(11): 2023 -2028 .
[8]	张鹏, 刘海峰, 陈贝凌, 唐青龙, 尧命发. 掺混含氧燃料的柴油替代物部分预混火焰中多环芳香烃的荧光光谱和碳烟浓度[J]. 物理化学学报, 2015, 31(1): 32 -40 .
[9]	何文英, 姚小军, 华英杰, 黄国雷, 吴秀丽, 李小宝, 韩长日, 宋小平. 考拉维酸对人血清白蛋白结构的影响[J]. 物理化学学报, 2014, 30(11): 2142 -2148 .
[10]	朱德华, 钟蓉, 曹宇, 彭志辉, 冯爱新, 向卫东, 赵家龙. CuInS₂量子点敏化太阳能电池中尺寸依赖的电子注入和光电性质[J]. 物理化学学报, 2014, 30(10): 1861 -1866 .
[11]	宁爱民, 孟磊, 赵仲麟, 郑先福, 宛新生. 牛血清白蛋白与十二烷基硫酸钠作用的机理[J]. 物理化学学报, 2013, 29(12): 2639 -2646 .
[12]	蒋礼林, 刘伟龙, 宋云飞, 何兴, 王阳, 吴红琳, 杨延强. 香豆素343敏化TiO₂纳米粒子光致电子转移的荧光和拉曼光谱[J]. 物理化学学报, 2012, 28(12): 2953 -2957 .
[13]	韩利娟, 叶仲斌, 陈洪, 罗平亚. 疏水缔合聚丙烯酰胺与双子表面活性剂的自组装[J]. 物理化学学报, 2012, 28(06): 1405 -1410 .
[14]	张建华, 刘琼, 陈玉苗, 刘兆清, 徐常威. 紫外-可见吸收光谱结合高斯多峰拟合技术测定甲基红酸离解常数[J]. 物理化学学报, 2012, 28(05): 1030 -1036 .
[15]	王艳艳, 姜艳霞, 沙德礼, 罗德礼, 孙世刚. 电化学和紫外-可见吸收光谱法研究pH和金纳米粒子对细胞色素c的影响[J]. 物理化学学报, 2012, 28(05): 1127 -1133 .

新型螺吡喃衍生物: 离子传感和分子水平的信息处理

New Spiropyran Derivatives: Ion Sensing and Information Processing at the Molecular Level

PDF

赞

可视化

摘要/Abstract

支持信息

引用本文

使用本文

参考文献

相关文章 15

Metrics

推荐阅读 0