Фталоцианины и нафталоцианины, замещенные функциональными группами, содержащими серу: синтез, получение гибридов с наночастицами золота и некоторые области применения
Аннотация
Представлены синтетические подходы к фталоцианинам, их полиядерным производным и сэндвичевым комплексам, замещенным функциональными группами, содержащими серу. Дополнительно рассмотрены комплексы, обладающие протяженной системой π-сопряжения (2,3-нафталоцианины плоского и сэндвичевого типа). Рассмотрены основные области применения данных соединений. Особое внимание уделяется образованию конъюгатов с наночастицами золота - перспективным материалам для органической электроники.
Литература
Chen Y., Li D., Yuan N., Gao J., Gu R., Lu G. and Bouvet M., Journal of Materials Chemistry, 2012, 22, 22142-22149.
https://doi.org/10.1039/c2jm35219b
Schlettwein D., Woehrle D., Karmann E. and Melville U., Chemistry of Materials, 1994, 6, 3-6.
https://doi.org/10.1021/cm00037a001
de la Torre G., Vázquez P., Agulló-López F. and Torres T., Chemical Reviews, 2004, 104, 3723-3750.
https://doi.org/10.1021/cr030206t
Khoza P. and Nyokong T., Journal of Molecular Catalysis A: Chemical, 2015, 399, 25-32.
https://doi.org/10.1016/j.molcata.2015.01.017
Lamch Ł., Tsirigotis-Maniecka M., Kulbacka J. and Wilk K. A., Arkivoc, 2017, part ii, 433-445.
https://doi.org/10.24820/ark.5550190.p009.764
Kimani S. G., Shmigol T. A., Hammond S., Phillips J. B., Bruce J. I., MacRobert A. J., Malakhov M. V. and Golding J. P., Photochemistry and Photobiology, 2013, 89, 139-149.
https://doi.org/10.1111/j.1751-1097.2012.01204.x
Pushkarev V. E., Tomilova L. G. and Nemykin V. N., Coordination Chemistry Reviews, 2016, 319, 110-179.
https://doi.org/10.1016/j.ccr.2016.04.005
Wang H., Qi D., Xie Z., Cao W., Wang K., Shang H. and Jiang J., Chemical Communications, 2013, 49, 889-891.
https://doi.org/10.1039/C2CC38088A
Wang H., Kobayashi N. and Jiang J., Chemistry - A European Journal, 2012, 18, 1047-1049.
https://doi.org/10.1002/chem.201103037
Wang H., Wang K., Bian Y., Jiang J. and Kobayashi N., Chemical Communications, 2011, 47, 6879-6881.
https://doi.org/10.1039/c1cc11190f
Wang H., Qian K., Wang K., Bian Y., Jiang J. and Gao S., Chemical Communications, 2011, 47, 9624-9626.
https://doi.org/10.1039/c1cc12509e
Gao S., Zhao H., Huo L. H., Zhao J. G., Wu Y. Q. and Xi S. Q., Sensors and Actuators B: Chemical, 2004, 97, 319-323.
https://doi.org/10.1016/j.snb.2003.09.007
Vagin S. and Hanack M., European Journal of Organic Chemistry, 2003, 2003, 2661-2669.
https://doi.org/10.1002/ejoc.200300062
Dubinina T. V., Tomilova L. G. and Zefirov N. S., Russian Chemical Reviews, 2013, 82, 865.
https://doi.org/10.1070/RC2013v082n09ABEH004353
Tolbin A. Y., Khabashesku V. N. and Tomilova L. G., Mendeleev Communications, 2012, 22, 59-61.
https://doi.org/10.1016/j.mencom.2012.03.001
Bottari G., de la Torre G. and Torres T., Accounts of Chemical Research, 2015, 48, 900-910.
https://doi.org/10.1021/ar5004384
Kotiaho A., Lahtinen R., Efimov A., Metsberg H.-K., Sariola E., Lehtivuori H., Tkachenko N. V. and Lemmetyinen H., The Journal of Physical Chemistry C, 2010, 114, 162-168.
https://doi.org/10.1021/jp9087173
Forteath S., Antunes E., Chidawanyika W. and Nyokong T., Polyhedron, 2012, 34, 114-120.
https://doi.org/10.1016/j.poly.2011.12.015
Nikitenko S. L., Spitsina N. G., Kaplunov M. G. and Tomilova L. G., Fullerenes, Nanotubes and Carbon Nanostructures, 2010, 19, 141-146.
https://doi.org/10.1080/1536383X.2010.490140
Martinez-Diaz M. V., de la Torre G. and Torres T., Chemical Communications, 2010, 46, 7090-7108.
https://doi.org/10.1039/c0cc02213f
Zasedatelev A. V., Dubinina T. V., Krichevsky D. M., Krasovskii V. I., Gak V. Y., Pushkarev V. E., Tomilova L. G. and Chistyakov A. A., The Journal of Physical Chemistry C, 2016, 120, 1816-1823.
https://doi.org/10.1021/acs.jpcc.5b08804
Hone D. C., Walker P. I., Evans-Gowing R., FitzGerald S., Beeby A., Chambrier I., Cook M. J. and Russell D. A., Langmuir, 2002, 18, 2985-2987.
https://doi.org/10.1021/la0256230
Manoto S.L., Oluwole D.O., Malabi R., Maphanga C., Ombinda-Lemboumba S., Nyokong T., Mthunzi-Kufa P. Optical Methods for Tumor Treatment and Detection: Mechanisms and Techniques in Photodynamic Therapy XXVI 2017, 1004716.
https://doi.org/10.1117/12.2252838
Teixeira R., Paulo P. M. R., Viana A. S. and Costa S. M. B., The Journal of Physical Chemistry C, 2011, 115, 24674-24680.
https://doi.org/10.1021/jp209605v
Kuzmina E. A., Dubinina T. V., Zasedatelev A. V., Baranikov A. V., Makedonskaya M. I., Egorova T. B. and Tomilova L. G., Polyhedron, 2017, 135, 41-48.
https://doi.org/10.1016/j.poly.2017.06.048
Beloglazkina E. K., Majouga A. G., Romashkina R. B., Zyk N. V. and Zefirov N. S., Russian Chemical Reviews, 2012, 81, 65.
https://doi.org/10.1070/RC2012v081n01ABEH004158
Tombe S., Chidawanyika W., Antunes E., Priniotakis G., Westbroek P. and Nyokong T., Journal of Photochemistry and Photobiology A: Chemistry, 2012, 240, 50-58.
https://doi.org/10.1016/j.jphotochem.2012.05.011
Daniel M.-C. and Astruc D., Chemical Reviews, 2004, 104, 293-346.
https://doi.org/10.1021/cr030698+
Lukyanets E. A. and Nemykin V. N., Journal of Porphyrins and Phthalocyanines, 2010, 14, 1-40.
https://doi.org/10.1142/S1088424610001799
Nemykin V. N. and Luk'yanets E. A., Arkivoc, 2010, i, 136-208.
https://doi.org/10.3998/ark.5550190.0011.104
Gobo N. R. S., Brocksom T. J., Zukerman-Schpector J. and de Oliveira K. T., European Journal of Organic Chemistry, 2013, 2013, 5028-5031.
https://doi.org/10.1002/ejoc.201300415
Bankole O. M., Yılmaz Y. and Nyokong T., Optical Materials, 2016, 51, 194-202.
https://doi.org/10.1016/j.optmat.2015.11.041
Poon K.-W., Liu W., Chan P.-K., Yang Q., Chan T. W. D., Mak T. C. W. and Ng D. K. P., The Journal of Organic Chemistry, 2001, 66, 1553-1559.
https://doi.org/10.1021/jo0004308
del Rey B., Keller U., Torres T., Rojo G., Agulló-López F., Nonell S., Martí C., Brasselet S., Ledoux I. and Zyss J., Journal of the American Chemical Society, 1998, 120, 12808-12817.
https://doi.org/10.1021/ja980508q
Tau P. and Nyokong T., Dalton Transactions, 2006, 4482-4490.
https://doi.org/10.1039/b607538j
Nombona N., Antunes E., Litwinski C. and Nyokong T., Dalton Transactions, 2011, 40, 11876-11884.
https://doi.org/10.1039/c1dt11151e
Gurol I., Ahsena V. and Bekaroglu O., Journal of the Chemical Society, Dalton Transactions, 1994, 497-500.
https://doi.org/10.1039/DT9940000497
Gurek A. G. and Bekaroglu O., Journal of the Chemical Society, Dalton Transactions, 1994, 1419-1423.
https://doi.org/10.1039/DT9940001419
Mayukh M., Sema C. M., Roberts J. M. and McGrath D. V., The Journal of Organic Chemistry, 2010, 75, 7893-7896.
https://doi.org/10.1021/jo1011637
Rey B., Martinez-Diaz M. V., Barbera J. and Torres T., Journal of Porphyrins and Phthalocyanines, 2000, 04, 569-573.
https://doi.org/10.1002/1099-1409(200008)4:5<569::AID-JPP273>3.0.CO;2-O
Hao Z., Wu X., Sun R., Ma C., Zhang X. ChemPhysChem 2012, 13, 267-273.
https://doi.org/10.1002/cphc.201100612
Kobayashi N., Ogata H., Nonaka N., Luk'yanets E.A. Chemistry - A European Journal 2003, 9, 5123-5134.
https://doi.org/10.1002/chem.200304834
Kobayashi N., Furuyama T., Satoh K. Journal of the American Chemical Society 2011, 133, 19642-19645.
https://doi.org/10.1021/ja208481q
Dupont J., de Souza R.F., Suarez P.A.Z. Chemical Reviews 2002, 102, 3667-3692.
https://doi.org/10.1021/cr010338r
Lo P.-C., Cheng D.Y.Y., Ng D.K.P. Synthesis 2005, 2005, 1141-1147.
Wasserscheid P., Keim W. Angewandte Chemie International Edition 2000, 39, 3772-3789.
https://doi.org/10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5
Al-Raqa S.Y. Journal of Porphyrins and Phthalocyanines 2006, 10, 55-62.
https://doi.org/10.1142/S1088424606000077
Miyaura N., Suzuki A. Chemical Reviews 1995, 95, 2457-2483.
https://doi.org/10.1021/cr00039a007
Dubinina T.V., Tychinsky P.I., Borisova N.E., Maklakov S.S., Sedova M.V., Kosov A.D., Tomilova L.G., Zefirov N.S. Dyes and Pigments 2017, 144, 41-47.
https://doi.org/10.1016/j.dyepig.2017.05.015
Eu S., Katoh T., Umeyama T., Matano Y., Imahori H. Dalton Transactions 2008, 5476-5483.
https://doi.org/10.1039/b803272f
Littke A.F., Fu G.C. Angewandte Chemie International Edition 2002, 41, 4176-4211.
https://doi.org/10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U
Littke A.F., Dai C., Fu G.C. Journal of the American Chemical Society 2000, 122, 4020-4028.
https://doi.org/10.1021/ja0002058
Dubinina T.V., Trashin S.A., Borisova N.E., Boginskaya I.A., Tomilova L.G., Zefirov N.S. Dyes and Pigments 2012, 93, 1471-1480.
https://doi.org/10.1016/j.dyepig.2011.10.012
Katayose M., Tai S., Kamijima K., Hagiwara H., Hayashi N. Journal of the Chemical Society, Perkin Transactions 2, 1992, 403-409.
https://doi.org/10.1039/p29920000403
Yeung Y.-O., Liu R. C. W., Law W.-F., Lau P.-L., Jiang J., Ng D.K.P. Tetrahedron 1997, 53, 9087-9096.
https://doi.org/10.1016/S0040-4020(97)00601-7
Kitahara K., Asano T., Hamano K.-i., Tokita S., Nishi H. Journal of Heterocyclic Chemistry 1990, 27, 2219-2220.
https://doi.org/10.1002/jhet.5570270766
Ng D. K. P., Yeung Y.-O., Chan W. K., Yu S.-C. Tetrahedron Letters 1997, 38, 6701-6704.
https://doi.org/10.1016/S0040-4039(97)01569-4
Dubinina T.V., Ivanov A.V., Borisova N.E., Trashin S.A., Gurskiy S.I., Tomilova L.G., Zefirov N.S. Inorganica Chimica Acta 2010, 363, 1869-1878.
https://doi.org/10.1016/j.ica.2010.02.011
Adams R., Reifschneider W., Ferretti A. In: Organic Syntheses, John Wiley & Sons, Inc., 1962, Vol. 42, p. 22.
Atilla D., Saydan N., Durmuş M., Gürek A.G., Khan T., Rück A., Walt H., Nyokong T., Ahsen V. Journal of Photochemistry and Photobiology A: Chemistry 2007, 186, 298-307.
https://doi.org/10.1016/j.jphotochem.2006.08.022
Atilla D., Gürek A.G., Basova T.V., Kiselev V.G., Hassan A., Sheludyakova L.A., Ahsen V. Dyes and Pigments 2011, 88, 280-289.
https://doi.org/10.1016/j.dyepig.2010.07.007
Basova T.V., Çamur M., Esenpınar A.A., Tuncel S., Hassan A., Alexeyev A., Banimuslem H., Durmuş M., Gürek A.G., Ahsen V. Synthetic Metals 2012, 162, 735-742.
https://doi.org/10.1016/j.synthmet.2012.02.006
Mbambisa G., Nyokong T. Polyhedron 2008, 27, 2799-2804.
https://doi.org/10.1016/j.poly.2008.06.004
Mbambisa G., Tau P., Antunes E., Nyokong T. Polyhedron 2007, 26, 5355-5364.
https://doi.org/10.1016/j.poly.2007.08.007
Lokesh K.S., Adriaens A. Dyes and Pigments 2013, 96, 269-277.
https://doi.org/10.1016/j.dyepig.2012.08.018
Dubinina T.V., Tychinsky P.I., Borisova N.E., Krasovskii V.I., Ivanov A.S., Savilov S.V., Maklakov S.S., Sedova M.V., Tomilova L.G. Dyes and Pigments 2018, 156, 386-394.
https://doi.org/10.1016/j.dyepig.2018.04.028
Zheng W., Wan C.-Z., Zhang J.-X., Li C.-H. and You X.-Z., Tetrahedron Letters, 2015, 56, 4459-4462.
https://doi.org/10.1016/j.tetlet.2015.05.086
Bankole O. M., Osifeko O. and Nyokong T., Journal of Photochemistry and Photobiology A: Chemistry, 2016, 329, 155-166.
https://doi.org/10.1016/j.jphotochem.2016.06.025
Chen Z., Niu L., Cheng Y., Zhou X., Zhong C., Zhang F. Dalton Transactions 2011, 40, 393-401.
https://doi.org/10.1039/C0DT01066A
Gülmez A.D., Polyakov M.S., Volchek V.V., Kostakoğlu S.T., Esenpinar A.A., Basova T.V., Durmuş M., Gürek A.G., Ahsen V., Banimuslem H.A., Hassan A.K. Sensors and Actuators B: Chemical 2017, 241, 364-375.
https://doi.org/10.1016/j.snb.2016.10.073
Oluwole D.O., Yagodin A.V., Britton J., Martynov A.G., Gorbunova Y.G., Tsivadze A.Y., Nyokong T. Dalton Transactions 2017, 46, 16190-16198.
https://doi.org/10.1039/C7DT03867D
Shokurov A.V., Yagodin A.V., Martynov A.G., Gorbunova Y.G., Selektor S.L. ECS Journal of Solid State Science and Technology 2020, 9, 051006.
https://doi.org/10.1149/2162-8777/ab9a5e
Chambrier I., Cook M.J., Russell D. A. Synthesis 1995, 1995, 1283-1286.
https://doi.org/10.1055/s-1995-4095
Lu G., Bai M., Li R., Zhang X., Ma C., Lo P.-C., Ng D.K.P., Jiang J. European Journal of Inorganic Chemistry 2006, 2006, 3703-3709.
https://doi.org/10.1002/ejic.200600295
Kandaz M., Bilgiçli A.T., Altındal A. Synthetic Metals 2010, 160, 52-60.
https://doi.org/10.1016/j.synthmet.2009.09.039
Yağlıoğlu H.G., Arslan M., Abdurrahmanoğlu Ş., Ünver H., Elmali A., Bekaroğlu Ö. Journal of Physics and Chemistry of Solids 2008, 69, 161-167.
https://doi.org/10.1016/j.jpcs.2007.08.012
Ban K., Nishizawa K., Ohta K., van de Craats A.M., Warman J.M., Yamamoto I., Shirai H. Journal of Materials Chemistry 2001, 11, 321-331.
https://doi.org/10.1039/b003984p
Gürek A.G., Basova T., Luneau D., Lebrun C., Kol'tsov E., Hassan A.K., Ahsen V. Inorganic Chemistry 2006, 45, 1667-1676.
https://doi.org/10.1021/ic051754n
Atilla D., Kilinç N., Yuksel F., Gürek A.G., Öztürk Z.Z., Ahsen V. Synthetic Metals 2009, 159, 13-21.
https://doi.org/10.1016/j.synthmet.2008.07.013
Kadish K.M., Nakanishi T., Gürek A., Ahsen V., Yilmaz I. The Journal of Physical Chemistry B 2001, 105, 9817-9821.
https://doi.org/10.1021/jp012636y
Magdesieva T.V., Zhukov I.V., Tomilova L.G., Korenchenko O.V., Kalashnikova I.P., Butin K.P. Russian Chemical Bulletin 2001, 50, 396-403.
https://doi.org/10.1023/A:1011340603115
Jiang J., Liu W., Poon K.-W., Du D., Arnold D.P., Ng D.K.P. European Journal of Inorganic Chemistry 2000, 2000, 205-209.
https://doi.org/10.1002/(SICI)1099-0682(200001)2000:1<205::AID-EJIC205>3.0.CO;2-1
Dubinina T.V., Piskovoi R.A., Tolbin A.Y., Pushkarev V.E., Vagin M.Y., Tomilova L.G., Zefirov N.S. Russian Chemical Bulletin, 2008, 57, 1912-1919.
https://doi.org/10.1007/s11172-008-0258-6
Dubinina T.V., Paramonova K.V., Trashin S.A., Borisova N.E., Tomilova L.G., Zefirov N.S. Dalton Transactions 2014, 43, 2799-2809.
https://doi.org/10.1039/C3DT52726C
Gorbunova Y.G., Lapkina L.A., Martynov A.G., Biryukova I.V., Tsivadze A.Y. Russian Journal of Coordination Chemistry 2004, 30, 245-251.
https://doi.org/10.1023/B:RUCO.0000022799.63314.fc
Alpugan S., Isci U., Albrieux F., Hirel C., Gurek A.G., Bretonniere Y., Ahsen V., Dumoulin F. Chemical Communications 2014, 50, 7466-7468.
https://doi.org/10.1039/c4cc02523g
Nyokong T., Furuya F., Kobayashi N., Du D., Liu W., Jiang J. Inorganic Chemistry 2000, 39, 128-135.
https://doi.org/10.1021/ic990483b
Abdurrahmanoğlu Ş., Altındal A., Bulut M., Bekaroğlu Ö. Polyhedron 2006, 25, 3639-3646.
https://doi.org/10.1016/j.poly.2006.07.036
Ceyhan T., Altındal A., Erbil M.K., Bekaroğlu Ö. Polyhedron 2006, 25, 737-746.
https://doi.org/10.1016/j.poly.2005.07.046
Abdurrahmanoglu S., Altindal A., Riza Ozkaya A., Bulut M., Bekaroglu O. Chemical Communications 2004, 2096-2097.
https://doi.org/10.1039/B406739H
Yilmaz I., Burkut Koçak M. Polyhedron 2004, 23, 1279-1285.
https://doi.org/10.1016/j.poly.2004.02.009
Gürek A.G., Bekaroglu Ö. Journal of Porphyrins and Phthalocyanines 1997, 1, 67-76.
https://doi.org/10.1002/(SICI)1099-1409(199701)1:1<67::AID-JPP8>3.0.CO;2-R
Ceyhan T., Altındal A., Özkaya A.R., Erbil M.K., Bekaroğlu Ö. Polyhedron 2007, 26, 73-84.
https://doi.org/10.1016/j.poly.2006.07.035
Ceyhan T., Korkmaz M., Erbil M.K., Bekaroğlu Ö. Journal of Porphyrins and Phthalocyanines 2005, 09, 423-429.
https://doi.org/10.1142/S1088424605000526
Şen P., Dumludağ F., Salih B., Özkaya A.R., Bekaroğlu Ö. Synthetic Metals 2011, 161, 1245-1254.
https://doi.org/10.1016/j.synthmet.2011.04.012
Noda Y., Noro S.-i., Akutagawa T., Nakamura T. Scientific Reports 2014, 4, 3758.
https://doi.org/10.1038/srep03758
Nwaji N., Oluwole D.O., Mack J., Louzada M., Khene S., Britton J., Nyokong T. Dyes and Pigments 2017, 140, 417-430.
https://doi.org/10.1016/j.dyepig.2017.01.066
Bankole O.M., Nyokong T. Journal of Photochemistry and Photobiology A: Chemistry 2016, 319, 8-17.
https://doi.org/10.1016/j.jphotochem.2015.12.014
Mayukh M., Macech M.R., Placencia D., Cao Y., Armstrong N.R., McGrath D.V. ACS Applied Materials & Interfaces 2015, 7, 23912-23919.
https://doi.org/10.1021/acsami.5b05900
Quartarolo A.D., Pérusse D., Dumoulin F., Russo N., Sicilia E. Journal of Porphyrins and Phthalocyanines 2013, 17, 980-988.
https://doi.org/10.1142/S1088424613500569
Yao Y., Chen W., Lu S., Zhao B. Dyes and Pigments 2007, 73, 217-223.
https://doi.org/10.1016/j.dyepig.2005.11.009
Ikeue T., Sonoda M., Kurahashi S., Tachibana H., Teraoka D., Sugimori T., Kasuga K., Handa M. Inorganic Chemistry Communications 2010, 13, 1170-1172.
https://doi.org/10.1016/j.inoche.2010.06.041
Yang J., Van De Mark M.R. Tetrahedron Letters 1993, 34, 5223-5226.
https://doi.org/10.1016/S0040-4039(00)73958-X
Zorlu Y., Kumru U., İşci Ü., Divrik B., Jeanneau E., Albrieux F., Dede Y., Ahsen V., Dumoulin F. Chemical Communications 2015, 51, 6580-6583.
https://doi.org/10.1039/C5CC01085C
Chen Y., Liu H.-G., Pan N., Jiang J. Thin Solid Films 2004, 460, 279-285.
