Abstract
In this chapter, we wish to review the recent progress in the application of phthalocyanines as functional molecular materials including (1) semiconducting materials for organic photovoltaic cells and organic field effect transistors, (2) functional organic dyes as photosensitizers for photodynamic therapy and dye-sensitized solar cells, and (3) single-molecule magnets. The structure–function relationship has been highlighted on the bases of selected examples since 2010, which hopefully will be informative for the future developments of phthalocyanine chemistry and related materials science.
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Leznoff CC, Lever ABP (eds) (1989) Phthalocyanines: properties and applications. VCH, Cambridge
McKeown NB (1998) Phthalocyanine materials: structure, synthesis and function. Cambridge University Press, Cambridge
Kadish KM, Smith KM, Guilard R (eds) (2003) Phthalocyanines: synthesis, vol 15, The porphyrin handbook. Academic, San Diego
Kadish KM, Smith KM, Guilard R (eds) (2003) Phthalocyanines: structural characterization, vol 20, The porphyrin handbook. Academic, San Diego
Kadish KM, Smith KM, Guiland R (eds) (2003) Phthalocyanines: spectroscopic and electrochemical characterization, vol 16, The porphyrin handbook. Academic, San Diego
Peumans P, Uchida S, Forrest SR (2003) Nature 425(6954):158–162
Horowitz G (1998) Adv Mater 10(5):365–377
Huang Q, Evmenenko GA, Dutta P, Lee P, Armstrong NR, Marks TJ (2005) J Am Chem Soc 127(29):10227–10242
Bonnett R (1995) Chem Soc Rev 24(1):19–33
He J, Benkoe G, Korodi F, Polivka T, Lomoth R, Kermark B, Sun L, Hagfeldt A, Sundstroem V (2002) J Am Chem Soc 124(17):4922–4932
Ishikawa N, Sugita M, Ishikawa T, Koshihara S, Kaizu Y (2003) J Am Chem Soc 125(29):8694–8695
de la Torre G, Vazquez P, Agullo-Lopez F, Torres T (2004) Chem Rev 104(9):3723–3750
Sorokin AB (2013) Chem Rev 113(10):8152–8191
Mele G, Del Sole R, Vasapollo G, Garcia-Lopez E, Palmisano L, Schiavello M (2003) J Catal 217(2):334–342
Reetz MT, Jiao N (2006) Angew Chem Int Ed 45(15):2416–2419
Zhang QM, Li H, Poh M, Xia F, Cheng ZY, Xu H, Huang C (2002) Nature 419(6904):284–287
Somani PR, Radhakrishnan S (2003) Mater Chem Phys 77(1):117–133
Gryko D, Li J, Diers JR, Roth KM, Bocian DF, Kuhr WG, Lindsey JS (2001) J Mater Chem 11(4):1162–1180
van Nostrum CF, Picken SJ, Schouten A, Nolte RJM (1995) J Am Chem Soc 117(40):9957–9965
Matsushita O, Derkacheva VM, Muranaka A, Shimizu S, Uchiyama M, Luk’Yanets EA, Kobayashi N (2012) J Am Chem Soc 134(7):3411–3418
Wang H, Qi D, Xie Z, Cao W, Wang K, Shang H, Jiang J (2013) Chem Commun 49(9):889–891
Bottari G, de la Torre G, Guldi DM, Torres T (2010) Chem Rev 110(11):6768–6816
Bottari G, de la Torre G, Torres T (2015) Acc Chem Res 48(4):900–910
Spitler EL, Dichtel WR (2010) Nat Chem 2(8):672–677
Imahori H, Umeyama T, Kurotobi K, Takano Y (2012) Chem Commun 48(34):4032–4045
de la Torre G, Claessens CG, Torres T (2007) Chem Commun 43(20):2000–2015
Abel M, Clair S, Ourdjini O, Mossoyan M, Porte L (2011) J Am Chem Soc 133(5):1203–1205
Baeg K, Binda M, Natali D, Caironi M, Noh Y (2013) Adv Mater 25(31):4267–4295
Urdampilleta M, Klyatskaya S, Cleuziou JP, Ruben M, Wernsdorfer W (2011) Nat Mater 10(7):502–506
Martinez-Diaz MV, de la Torre G, Torres T (2010) Chem Commun 46(38):7090–7108
Walter MG, Rudine AB, Wamser CC (2010) J Porphyrins Phthalocyanines 14(9):759–792
Wang X, Tamiaki H (2010) Energy Environ Sci 3(1):94–106
Bottari G, Trukhina O, Ince M, Torres T (2012) Coord Chem Rev 256(21–22):2453–2477
Ragoussi M, Ince M, Torres T (2013) Eur J Org Chem 2013(29):6475–6489
Singh VK, Kanaparthi RK, Giribabu L (2014) RSC Adv 4(14):6970–6984
Martin-Gomis L, Fernandez-Lazaro F, Sastre-Santos A (2014) J Mater Chem A 2(38):15672–15682
Imahori H, Kurotobi K, Walter MG, Rudine AB, Wamser CC (2012) Porphyrin and phthalocyanine based solar cells. In: Kadish KM, Smith KM, Guilard R (eds) Handbook of porphyrin science, vol 18. World Scientific, Singapore, pp 57–121
Kesters J, Verstappen P, Kelchtermans M, Lutsen L, Vanderzande D, Maes W (2015) Adv Energy Mater. doi:10.1002/aenm.201500218
Trogler WC (2012) Struct Bond 142:91–118
Bill NL, Trukhina O, Sessler JL, Torres T (2015) Chem Commun 51(37):7781–7794
Rodriguez-Mendez ML, Apetrei C, Medina-Plaza C, Munoz R, de Saja JA (2014) Sensor arrays based on phthalocyanines: new developments on nanostructured and biomimetic electrochemical sensors. In: Lvova L, Kirsanov D, Di Natale C, Legin A (eds) Multisensor systems for chemical analysis. Pan Stanford, Singapore, pp 139–179. doi:10.1201/b15491-5
Josefsen LB, Boyle RW (2012) Theranostics 2(9):916–966
Ishii K (2012) Coord Chem Rev 256(15–16):1556–1568
Sekkat N, van den Bergh H, Nyokong T, Lange N (2012) Molecules 17:98–144
Ali H, van Lier JE (2010) Porphyrins and phthalocyanines as photosensitizers and radiosensitizers. In: Kadish KM, Smith KM, Guilard R (eds) Handbook of porphyrin science, vol 4. World Scientific, Singapore, pp 1–119
Nyokong T (2011) Pure Appl Chem 83(9):1763–1779
Pietrangeli D, Rosa A, Ristori S, Salvati A, Altieri S, Ricciardi G (2013) Coord Chem Rev 257(15–16):2213–2231
Jiang Z, Shao J, Yang T, Wang J, Jia L (2014) J Pharm Biomed 87:98–104
Sergeeva NN, Senge MO (2012) Photochemical transformations involving porphyrins and phthalocyanines. In: Griesbeck A, Oelgemoller M, Ghetti F (eds) CRC handbook of organic photochemistry and photobiology, vol 1, 3rd edn. CRC, Boca Raton, pp 831–879. doi:10.1201/b12252-35
Ding L, Luan L, Shi J, Liu W (2013) Wuji Huaxue Xuebao 29(8):1591–1598, In Chinese
Komeda T, Katoh K, Yamashita M (2014) Prog Surf Sci 89(2):127–160
Chen J, Wang S, Yang G (2015) Wuli Huaxue Xuebao 31(4):595–611, In Chinese
Venugopal Rao S (2012) Proc SPIE 8434(Nonlinear Optics and Applications VI):84341B
Zagal JH, Griveau S, Silva JF, Nyokong T, Bedioui F (2010) Coord Chem Rev 254(23–24):2755–2791
Sorokin AB, Kudrik EV (2010) Catal Today 159(1):37–46
Kadish KM, Smith KM, Guilard R (eds) (2010) Electronic absorption spectra-phthalocyanines, vol 9, Handbook of porphyrin science. World Scientific, Singapore
Bian Y, Zhang Y, Ou Z, Jiang J (2011) Chemistry of sandwich tetrapyrrole rare earth complexes. In: Kadish KM, Smith KM, Guilard R (eds) Handbook of porphyrin science, vol 14. World Scientific, Singapore, pp 249–460
Ragoussi M, Torres T (2014) Chem Asian J 9(10):2676–2707
Mack J, Kobayashi N (2011) Chem Rev 111(2):281–321
Dumoulin F, Ahsen V (2011) J Porphyrins Phthalocyanines 15(7–8):481–504
Cook MJ, Chambrier I (2011) J Porphyrins Phthalocyanines 15(3):149–173
Gorbunova YG, Martynov AG, Tsivadze AY (2012) Crown-substituted phthalocyanines. From synthesis towards materials. In: Kadish KM, Smith KM, Guilard R (eds) Handbook of porphyrin science, vol 24. World Scientific, Singapore, pp 271–388
Figueira F, Pereira PMR, Silva S, Cavaleiro JAS, Tome JPC (2014) Curr Org Synth 11(1):110–126
Kobayashi N (2012) Synthesis and characterization of chiral phthalocyanines. In: Kadish KM, Smith KM, Guilard R (eds) Handbook of porphyrin science, vol 23. World Scientific, Singapore, pp 373–440
Jiang J (2010) Functional phthalocyanine molecular materials. In: Mingos M (ed) Structure bonding, vol 135. Springer, Berlin. doi:10.1007/978-3-642-04752-7
Nyokong T (2010) Struct Bond 135:45–88
Luo Q, Liu Y, Tian H (2010) Struct Bond 135:89–104
Bekaroglu O (2010) Struct Bond 135:105–136
Liu J, Lo P, Ng DKP (2010) Struct Bond 135:169–210
de la Torre G, Bottari G, Hahn U, Torres T (2010) Struct Bond 135:1–44
Yoshimoto S, Kobayashi N (2010) Struct Bond 135:137–168
Zhang Y, Cai X, Bian Y, Jiang J (2010) Struct Bond 135:275–322
Li X, Wang H, Wu H (2010) Struct Bond 135:229–274
Ishikawa N (2010) Struct Bond 135:211–228
Tang CW (1986) Appl Phys Lett 48(2):183–185
Osedach TP, Andrew TL, Bulović V (2013) Energy Environ Sci 6(3):711–718
Xu Z, Roy VAL, Low K, Che C (2011) Chem Commun 47(34):9654–9656
Qu D, Guo R, Yue S, Wu Y, Yan P, Cheng G (2014) J Phys D 47(41):415104
Meiss J, Merten A, Hein M, Schuenemann C, Schäfer S, Tietze M, Uhrich C, Pfeiffer M, Leo K, Riede M (2012) Adv Funct Mater 22(2):405–414
Brendel M, Krause S, Steindamm A, Topczak AK, Sundarraj S, Erk P, Höhla S, Fruehauf N, Koch N, Pflaum J (2015) Adv Funct Mater 25(10):1565–1573
Beaumont N, Hancox I, Sullivan P, Hatton RA, Jones TS (2011) Energy Environ Sci 4(5):1708–1711
Zhong S, Zhong JQ, Wang XZ, Huang MY, Qi DC, Chen ZK, Chen W (2012) J Phys Chem C 116(3):2521–2526
Verreet B, Müller R, Rand BP, Vasseur K, Heremans P (2011) Org Electron 12(12):2131–2139
Vasseur K, Rand BP, Cheyns D, Froyen L, Heremans P (2011) Chem Mater 23(3):886–895
Vasseur K, Rand BP, Cheyns D, Temst K, Froyen L, Heremans P (2012) J Phys Chem Lett 3(17):2395–2400
Suzuki A, Furukawa R, Akiyama T, Oku T (2015) AIP Conf Proc 1649(1, Irago Conference 2014):107–112
Hori T, Fukuoka N, Masuda T, Miyake Y, Yoshida H, Fujii A, Shimizu Y, Ozaki M (2011) Sol Energy Mater Sol Cells 95(11):3087–3092
Varotto A, Nam C, Radivojevic I, Tomé JPC, Cavaleiro JAS, Black CT, Drain CM (2010) J Am Chem Soc 132(8):2552–2554
Jurow MJ, Hageman BA, DiMasi E, Nam C, Pabon C, Black CT, Drain CM (2013) J Mater Chem A 1(5):1557–1565
Fischer MKR, López-Duarte I, Wienk MM, Martínez-Díaz MV, Janssen RAJ, Bäuerle P, Torres T (2009) J Am Chem Soc 131(24):8669–8676
Schumann S, Hatton RA, Jones TS (2011) J Phys Chem C 115(11):4916–4921
Ryan JW, Anaya-Plaza E, Escosura ADL, Torres T, Palomares E (2012) Chem Commun 48(49):6094–6096
Jiang J, Ng DKP (2009) Acc Chem Res 42(1):79–88
Videlot C, Fichou D, Garnier F (1998) Mol Cryst Liq Cryst Sci Technol Sect A 322(1):319–328
Liu L, Hu AT (2003) J Porphyrins Phthalocyanines 7(8):565–571
Liu MO, Hu AT (2004) J Organomet Chem 689(15):2450–2455
Wang Q, Li Y, Yan X, Rathi M, Ropp M, Galipeau D, Jiang J (2008) Appl Phys Lett 93(7):73303
Li Y, Bian Y, Yan M, Thapaliya PS, Johns D, Yan X, Galipeau D, Jiang J (2011) J Mater Chem 21(30):11131–11141
Tsumura A, Koezuka H, Ando T (1986) Appl Phys Lett 49(18):1210
Gao X, Zhao Z (2015) Sci China Chem 58(6):947–968
Mei J, Diao Y, Appleton AL, Fang L, Bao Z (2013) J Am Chem Soc 135(18):6724–6746
Wang C, Dong H, Hu W, Liu Y, Zhu D (2012) Chem Rev 112(4):2208–2267
Murphy AR, Fréchet JMJ (2007) Chem Rev 107(4):1066–1096
Melville OA, Lessard BH, Bender TP (2015) ACS Appl Mater Interfaces 7(24):13105–13118
Li L, Tang Q, Li H, Hu W, Yang X, Shuai Z, Liu Y, Zhu D (2008) Pure Appl Chem 80(11):2231–2240
Guillaud G, Madru R, Sadoun MA, Maitrot M (1989) J Appl Phys 66(9):4554
Li L, Tang Q, Li H, Yang X, Hu W, Song Y, Shuai Z, Xu W, Liu Y, Zhu D (2007) Adv Mater 19(18):2613–2617
Shaymurat T, Tang Q, Tong Y, Dong L, Liu Y (2013) Adv Mater 25(16):2269–2273
Huang W, Sinha J, Yeh M, Hardigree JFM, LeCover R, Besar K, Rule AM, Breysse PN, Katz HE (2013) Adv Funct Mater 23(33):4094–4104
Fernandes EGR, Vieira NCS, de Queiroz AAA, Guimarães FEG, Zucolotto V (2010) J Phys Chem C 114(14):6478–6483
Sun L, Zhang J, Zhao F, Luo X, Lv W, Li Y, Ren Q, Wen Z, Peng Y, Liu X (2015) Nanotechnology 26(18):185501
Zhang L, Wang H, Zhao Y, Guo Y, Hu W, Yu G, Liu Y (2013) Adv Mater 25(38):5455–5460
Maheshwari P, Mukherjee S, Bhattacharya D, Sen S, Tokas RB, Honda Y, Basu S, Padma N, Pujari PK (2015) ACS Appl Mater Interfaces 7(19):10169–10177
Jung JS, Lee JW, Kim K, Cho MY, Jo SG, Joo J (2010) Chem Mater 22(7):2219–2225
Su Y, Wang C, Xie W, Xie F, Chen J, Zhao N, Xu J (2011) ACS Appl Mater Interfaces 3(12):4662–4667
Deng W, Zhang X, Wang J, Shang Q, Gong C, Zhang X, Zhang Q, Jie J (2014) Org Electron 15(7):1317–1323
Liu W, Jackson BL, Zhu J, Miao C, Chung C, Park YJ, Sun K, Woo J, Xie Y (2010) ACS Nano 4(7):3927–3932
Luo X, Li Y, Lv W, Zhao F, Sun L, Peng Y, Wen Z, Zhong J, Zhang J (2015) Nanotechnology 26(3):35201
Cao L, Chen S, Wei D, Liu Y, Fu L, Yu G, Liu H, Liu X, Wu D (2010) J Mater Chem 20(12):2305–2309
Jiang L, Dong H, Meng Q, Tan J, Jiang W, Xu C, Wang Z, Hu W (2012) Adv Mater 24(5):694–698
Ward JW, Lamport ZA, Jurchescu OD (2015) ChemPhysChem 16(6):1118–1132
Cao Y, Wei Z, Liu S, Gan L, Guo X, Xu W, Steigerwald ML, Liu Z, Zhu D (2010) Angew Chem Int Ed 49(36):6319–6323
Pan F, Tian H, Qian X, Huang L, Geng Y, Yan D (2011) Org Electron 12(8):1358–1363
Huang L, Zhu F, Liu C, Treske U, Grobosch M, Tian H, Zhang J, Geng Y, Knupfer M, Yan D (2012) Adv Funct Mater 22(21):4598–4607
Dong S, Tian H, Huang L, Zhang J, Yan D, Geng Y, Wang F (2011) Adv Mater 23(25):2850–2854
Dong S, Bao C, Tian H, Yan D, Geng Y, Wang F (2013) Adv Mater 25(8):1165–1169
Chen Y, Su W, Bai M, Jiang J, Li X, Liu Y, Wang L, Wang S (2005) J Am Chem Soc 127(45):15700–15701
Su W, Jiang J, Xiao K, Chen Y, Zhao Q, Yu G, Liu Y (2005) Langmuir 21(14):6527–6531
Chen Y, Li R, Wang R, Ma P, Dong S, Gao Y, Li X, Jiang J (2007) Langmuir 23(25):12549–12554
Li R, Ma P, Dong S, Zhang X, Chen Y, Li X, Jiang J (2007) Inorg Chem 46(26):11397–11404
Gao Y, Ma P, Chen Y, Zhang Y, Bian Y, Li X, Jiang J, Ma C (2009) Inorg Chem 48(1):45–54
Ma P, Chen Y, Sheng N, Bian Y, Jiang J (2009) Eur J Inog Chem 2009(7):954–960
Chaure NB, Sosa-Sanchez JL, Cammidge AN, Cook MJ, Ray AK (2010) Org Electron 11(3):434–438
Bao Z, Lovinger AJ, Brown J (1998) J Am Chem Soc 120(1):207–208
Keil C, Schlettwein D (2011) Org Electron 12(8):1376–1382
Jiang H, Ye J, Hu P, Wei F, Du K, Wang N, Ba T, Feng S, Kloc C (2014) Sci Rep 4:7573
Song D, Zhu F, Yu B, Huang L, Geng Y, Yan D (2008) Appl Phys Lett 75(14):143303
Song D, Wang H, Zhu F, Yang J, Tian H, Geng Y, Yan D (2008) Adv Mater 20(11):2142–2144
Md Obaidulla SK, Goswami DK, Giri PK (2014) Appl Phys Lett 104(21):213302
Ma P, Kan J, Zhang Y, Hang C, Bian Y, Chen Y, Kobayshi N, Jiang J (2011) J Mater Chem 21(46):18552–18559
Zaumseil J, Sirringhaus H (2007) Chem Rev 107(4):1296–1323
Bisri SZ, Piliego C, Gao J, Loi MA (2014) Adv Mater 26(8):1176–1199
Zhang Y, Dong H, Tang Q, Ferdous S, Liu F, Mannsfeld SCB, Hu W, Briseno AL (2010) J Am Chem Soc 132(33):11580–11584
Fujimoto T, Matsushita MM, Awaga K (2013) J Phys Chem C 117(11):5552–5557
Nénon S, Kanehira D, Yoshimoto N, Fages F, Videlot-Ackermann C (2011) Synth Met 161(17–18):1915–1920
Opitz A, Bronner M, Bruetting W, Himmerlich M, Schaefer JA, Krischok S (2007) Appl Phys Lett 90(21):212111–212112
Kraus M, Richler S, Opitz A, Brutting W, Haas S, Hasegawa T, Hinderhofer A, Schreiber F (2010) J Appl Phys 107(9):94503
Kraus M, Haug S, Bruetting W, Opitz A (2011) Org Electron 12(5):731–735
Opitz A, Horlet M, Kiwull M, Wagner J, Kraus M, Bruetting W (2012) Org Electron 13(9):1614–1622
Yasuda T, Tsutsui T (2006) Jpn J Appl Phys 45(6L):L595
Zhong A, Bian Y, Zhang Y (2010) J Phys Chem C 114(7):3248–3255
Peng Y, Gao P, Lv W, Yao B, Fan G, Chen D, Xie J, Zhou M, Li Y, Wang Y (2013) IEEE Photon Technol Lett 25(22):2149–2152
Hayashi H, Nihashi W, Umeyama T, Matano Y, Seki S, Shimizu Y, Imahori H (2011) J Am Chem Soc 133(28):10736–10739
Shi Y, Li X (2014) Org Electron 15(1):286–293
Guillaud G, Al Sadoun M, Maitrot M, Simon J, Bouvet M (1990) Chem Phys Lett 167(6):503–506
Zhang Y, Cai X, Qi D, Bian Y, Jiang J (2008) J Phys Chem C 112(37):14579–14588
Chen Y, Li D, Yuan N, Gao J, Gu R, Lu G, Bouvet M (2012) J Mater Chem 22(41):22142–22149
Kong X, Jia Q, Wu F, Chen Y (2015) Dyes Pigments 115:67–72
Kan J, Chen Y, Qi D, Liu Y, Jiang J (2012) Adv Mater 24(13):1755–1758
Li D, Wang H, Kan J, Lu W, Chen Y, Jiang J (2013) Org Electron 14(10):2582–2589
Kong X, Zhang X, Gao D, Qi D, Chen Y, Jiang J (2015) Chem Sci 6(3):1967–1972
Zhang X, Chen Y (2014) Inorg Chem Commun 39:79–82
Gao D, Zhang X, Kong X, Chen Y, Jiang J (2015) ACS Appl Mater Interfaces 7(4):2486–2493
O’Regan B, Gratzel M (1991) Nature 353(6346):737–740
Hardin BE, Snaith HJ, McGehee MD (2012) Nat Photonics 6(3):162–169
Han L, Islam A, Chen H, Malapaka C, Chiranjeevi B, Zhang S, Yang X, Yanagida M (2012) Energy Environ Sci 5(3):6057–6060
Li L, Diau EW (2013) Chem Soc Rev 42(1):291–304
Mathew S, Yella A, Gao P, Humphry-Baker R, Curchod BFE, Ashari-Astani N, Tavernelli I, Rothlisberger U, Nazeeruddin MK, Grätzel M (2014) Nat Chem 6(3):242–247
Nazeeruddin MK, Humphry-Baker R, Grätzel M, Wöhrle D, Schnurpfeil G, Schneider G, Hirth A, Ttombach N (1999) J Porphyrins Phthalocyanines 03(03):230–237
Zhang L, Cole JM (2015) ACS Appl Mater Interfaces 7:3427–3455
Sharma D, Steen G, Korterik JP, García-Iglesias M, Vázquez P, Torres T, Herek JL, Huijser A (2013) J Phys Chem C 117(48):25397–25404
Lim B, Margulis GY, Yum J, Unger EL, Hardin BE, Grätzel M, McGehee MD, Sellinger A (2013) Org Lett 15(4):784–787
Radivojevic I, Bazzan G, Burton-Pye BP, Ithisuphalap K, Saleh R, Durstock MF, Francesconi LC, Drain CM (2012) J Phys Chem C 116(30):15867–15877
Hayat A, Shivashimpi GM, Nishimura T, Fujikawa N, Ogomi Y, Yamaguchi Y, Pandey SS, Ma T, Hayase S (2015) Appl Phys Express 8(4):47001. doi:10.7567/APEX.8.047001
Barea EM, Ortiz J, Payá FJ, Fernández-Lázaro F, Fabregat-Santiago F, Sastre-Santos A, Bisquert J (2010) Energy Environ Sci 3(12):1985–1994
Li R, Zhang X, Zhu P, Ng DKP, Kobayashi N, Jiang J (2006) Inorg Chem 45(5):2327–2334
Cid J, Yum J, Jang S, Nazeeruddin MK, Martínez-Ferrero E, Palomares E, Ko J, Grätzel M, Torres T (2007) Angew Chem Int Ed 46(44):8358–8362
Cid J, García-Iglesias M, Yum J, Forneli A, Albero J, Martínez-Ferrero E, Vázquez P, Grätzel M, Nazeeruddin MK, Palomares E, Torres T (2009) Chem Eur J 15(20):5130–5137
Garcia-Iglesias M, Cid J, Yum J, Forneli A, Vazquez P, Nazeeruddin MK, Palomares E, Gratzel M, Torres T (2011) Energy Environ Sci 4(1):189–194
García-Iglesias M, Yum J, Humphry-Baker R, Zakeeruddin SM, Péchy P, Vázquez P, Palomares E, Grätzel M, Nazeeruddin MK, Torres T (2011) Chem Sci 2(6):1145–1150
Ragoussi M, Cid J, Yum J, de la Torre G, Di Censo D, Grätzel M, Nazeeruddin MK, Torres T (2012) Angew Chem Int Ed 51(18):4375–4378
Ragoussi M, Yum J, Chandiran AK, Ince M, de la Torre G, Grätzel M, Nazeeruddin MK, Torres T (2014) ChemPhysChem 15(6):1033–1036
Mori S, Nagata M, Nakahata Y, Yasuta K, Goto R, Kimura M, Taya M (2010) J Am Chem Soc 132(12):4054–4055
Kimura M, Nomoto H, Masaki N, Mori S (2012) Angew Chem Int Ed 51(18):4371–4374
Kimura M, Nomoto H, Suzuki H, Ikeuchi T, Matsuzaki H, Murakami TN, Furube A, Masaki N, Griffith MJ, Mori S (2013) Chem Eur J 19(23):7496–7502
Ikeuchi T, Nomoto H, Masaki N, Griffith MJ, Mori S, Kimura M (2014) Chem Commun 50(16):1941–1943
Yu L, Zhou X, Yin Y, Liu Y, Li R, Peng T (2012) ChemPlusChem 77(11):1022–1027
Yu L, Shi W, Lin L, Liu Y, Li R, Peng T, Li X (2014) Dalton Trans 43(22):8421–8430
Lin L, Peng B, Shi W, Guo Y, Li R (2015) Dalton Trans 44(12):5867–5874
Yu L, Shi W, Lin L, Guo Y, Li R, Peng T (2015) Dyes Pigments 114:231–238
Yu L, Fan K, Duan T, Chen X, Li R, Peng T (2014) ACS Sustain Chem Eng 2(4):718–725
Ince M, Medina A, Yum J, Yella A, Claessens CG, Martínez-Díaz MV, Grätzel M, Nazeeruddin MK, Torres T (2014) Chem Eur J 20(7):2016–2021
Li Y, Lu P, Yan X, Jin L, Peng Z (2013) RSC Adv 3(2):545–558
Yamamoto S, Mori S, Wagner P, Mozer AJ, Kimura M (2015) Isr J Chem. doi:10.1002/ijch.201500023
Ethirajan M, Chen Y, Joshi P, Pandey RK (2011) Chem Soc Rev 40(1):340–362
Yuan A, Wu J, Tang X, Zhao L, Xu F, Hu Y (2013) J Pharm Sci 102(1):6–28
Zorlu Y, Dumoulin F, Durmuş M, Ahsen V (2010) Tetrahedron 66(17):3248–3258
Chen X, Li Y, Wang A, Zhou L, Lu S, Zhou J, Lin Y, Wei S (2015) Dyes Pigments 114:93–104
Machacek M, Cidlina A, Novakova V, Svec J, Rudolf E, Miletin M, Kučera R, Simunek T, Zimcik P (2015) J Med Chem 58(4):1736–1749
Liu W, Jensen TJ, Fronczek FR, Hammer RP, Smith KM, Vicente MGH (2005) J Med Chem 48(4):1033–1041
Luan L, Ding L, Zhang W, Shi J, Yu X, Liu W (2013) Bioorg Med Chem Lett 23(13):3775–3779
Lu S, Ma YJ, Xuan HY, Wang A, Zhao B, Li XD, Zhou JH, Lin Y, Zhou L, Wei SH (2014) RSC Adv 4(104):59759–59763
Bai M, Lo P, Ye J, Wu C, Fong W, Ng DKP (2011) Org Biomol Chem 9(20):7028–7032
Duan W, Lo P, Duan L, Fong W, Ng DKP (2010) Bioorg Med Chem 18(7):2672–2677
He H, Lo P, Ng DKP (2014) Chem Eur J 20(21):6241–6245
Ke M, Yeung S, Fong W, Ng DKP, Lo P (2012) Chem Eur J 18(14):4225–4233, S4221-S4225
Ke M, Ng DKP, Lo P (2014) Chem Asian J 9(2):554–561
Zhang FL, Huang Q, Zheng K, Li J, Liu JY, Xue JP (2013) Chem Commun 49(83):9570–9572
Zhang F, Huang Q, Liu J, Huang M, Xue J (2015) ChemMedChem 10(2):312–320
Lau JTF, Lo P, Fong W, Ng DKP (2012) J Med Chem 55(11):5446–5454
Luan L, Ding L, Shi J, Fang W, Ni Y, Liu W (2014) Chem Asian J 9(12):3491–3497
Lau JTF, Lo P, Fong W, Ng DKP (2011) Chem Eur J 17(27):7569–7577
Lau JTF, Lo P, Tsang Y, Fong W, Ng DKP (2011) Chem Commun 47(34):9657–9659
Chan CMH, Lo P, Yeung S, Ng DKP, Fong W (2010) Cancer Biol Ther 10(2):126–134
Jiang X, Lo P, Tsang Y, Yeung S, Fong W, Ng DKP (2010) Chem Eur J 16(16):4777–4783
Jiang X, Yeung S, Lo P, Fong W, Ng DKP (2011) J Med Chem 54(1):320–330
Jiang X, Lo P, Yeung S, Fong W, Ng DKP (2010) Chem Commun 46(18):3188–3190
Lau JTF, Lo P, Jiang X, Wang Q, Ng DKP (2014) J Med Chem 57(10):4088–4097
Mew D, Wat CK, Towers GH, Levy JG (1983) J Immunol 130(3):1473–1477
Hayley P, Stamati I, Yahioglu G, Butt M, Deonarain M (2013) Antibodies 2(2):270–305
Mitsunaga M, Ogawa M, Kosaka N, Rosenblum LT, Choyke PL, Kobayashi H (2011) Nat Med 17(12):1685–1691
Sano K, Mitsunaga M, Nakajima T, Choyke PL, Kobayashi H (2013) J Nucl Med 54(5):770–775
Nakajima T, Sano K, Choyke PL, Kobayashi H (2013) Theranostics 3(6):357–365
Sato K, Nagaya T, Mitsunaga M, Choyke PL, Kobayashi H (2015) Cancer Lett 365(1):112–121
Maawy AA, Hiroshima Y, Zhang Y, Heim R, Makings L, Garcia-Guzman M, Luiken GA, Kobayashi H, Hoffman RM, Bouvet M (2015) PLoS One 10(3):e121989
Chen Z, Xu P, Chen J, Chen H, Hu P, Chen X, Lin L, Huang Y, Zheng K, Zhou S, Li R, Chen S, Liu J, Xue J, Huang M (2014) Acta Biomater 10(10):4257–4268
Li R, Zheng K, Hu P, Chen Z, Zhou S, Chen J, Yuan C, Chen S, Zheng W, Ma E, Zhang F, Xue J, Chen X, Huang M (2014) Theranostics 4(6):642–659
Zhou X, Zheng K, Li R, Chen Z, Yuan C, Hu P, Chen J, Xue J, Huang M (2015) Acta Biomater 23:116–126
Gao D, Gao L, Zhang C, Liu H, Jia B, Zhu Z, Wang F, Liu Z (2015) Biomater 53:229–238
Moghimi SM, Hunter AC, Murray JC (2005) FASEB J 19(3):311–330
Kim BYS, Rutka JT, Chan WCW (2010) New Engl J Med 363(25):2434–2443
Zhao B, Duan W, Lo P, Duan L, Wu C, Ng DKP (2013) Chem Asian J 8(1):55–59
Hota R, Baek K, Yun G, Kim Y, Jung H, Park KM, Yoon E, Joo T, Kang J, Park CG, Bae SM, Ahn WS, Kim K (2013) Chem Sci 4(1):339–344
Jang W, Yim D, Hwang I (2014) J Mater Chem B 2(16):2202–2211
Master AM, Rodriguez ME, Kenney ME, Oleinick NL, Gupta AS (2010) J Pharm Sci 99(5):2386–2398
Liang R, Ma L, Zhang L, Li C, Liu W, Wei M, Yan D, Evans DG, Duan X (2014) Chem Commun 50(95):14983–14986
Taratula O, Schumann C, Duong T, Taylor KL, Taratula O (2015) Nanoscale 7(9):3888–3902
Brasch M, de la Escosura A, Ma Y, Uetrecht C, Heck AJR, Torres T, Cornelissen JJLM (2011) J Am Chem Soc 133(18):6878–6881
Nyokong T, Antunes E (2013) Coord Chem Rev 257(15–16):2401–2418
Camerin M, Magaraggia M, Soncin M, Jori G, Moreno M, Chambrier I, Cook MJ, Russell DA (2010) Eur J Cancer 46(10):1910–1918
Jang B, Park J, Tung C, Kim I, Choi Y (2011) ACS Nano 5(2):1086–1094
Cheng Y, Samia AC, Li J, Kenney ME, Resnick A, Burda C (2010) Langmuir 26(4):2248–2255
Obaid G, Chambrier I, Cook MJ, Russell DA (2012) Angew Chem Int Ed 51(25):6158–6162
Stuchinskaya T, Moreno M, Cook MJ, Edwards DR, Russell DA (2011) Photochem Photobiol Sci 10(5):822–831
Obaid G, Chambrier I, Cook MJ, Russell DA (2015) Photochem Photobiol Sci 14(4):737–747
Guo H, Qian H, Idris NM, Zhang Y (2010) Nanomed Nanotechnol Biol Med 6(3):486–495
Cui S, Chen H, Zhu H, Tian J, Chi X, Qian Z, Achilefu S, Gu Y (2012) J Mater Chem 22(11):4861
Cui S, Yin D, Chen Y, Di Y, Chen H, Ma Y, Achilefu S, Gu Y (2013) ACS Nano 7(1):676–688
Wang F, Chen X, Zhao Z, Tang S, Huang X, Lin C, Cai C, Zheng N (2011) J Mater Chem 21(30):11244–11252
Abramczyk H, Brozek-Pluska B, Surmacki J, Musial J, Kordek R (2014) Analyst 139(21):5547–5559
Giuliani F, Martinelli M, Cocchi A, Arbia D, Fantetti L, Roncucci G (2010) Antimicrob Agents Chemother 54(2):637–642
Ke M, Eastel JM, Ngai KLK, Cheung Y, Chan PKS, Hui M, Ng DKP, Lo P (2014) Eur J Med Chem 84:278–283
Ke M, Eastel JM, Ngai KLK, Cheung Y, Chan PKS, Hui M, Ng DKP, Lo P (2014) Chem Asian J 9(7):1868–1875
Mathew S, Murakami T, Nakatsuji H, Okamoto H, Morone N, Heuser JE, Hashida M, Imahori H (2013) ACS Nano 7(10):8908–8916
Sessoli R, Gatteschi D, Caneschi A, Novak MA (1993) Nature 365(6442):141–143
Gatteschi D, Sessoli R (2003) Angew Chem Int Ed 42(3):268–297
Wang H, Wang B, Bian Y, Gao S, Jiang J (2016) Coord Chem Rev 306:195–216. doi:10.1016/j.ccr.2015.07.004
Fukuda T, Shigeyoshi N, Yamamura T, Ishikawa N (2014) Inorg Chem 53(17):9080–9086
Gonidec M, Davies ES, McMaster J, Amabilino DB, Veciana J (2010) J Am Chem Soc 132(6):1756–1757
Gonidec M, Krivokapic I, Vidal-Gancedo J, Davies ES, McMaster J, Gorun SM, Veciana J (2013) Inorg Chem 52(8):4464–4471
Gonidec M, Amabilino DB, Veciana J (2012) Dalton Trans 41(44):13632–13639
Waters M, Moro F, Krivokapic I, McMaster J, Slageren JV (2012) Dalton Trans 41(4):1128–1130
Glebe U, Weidner T, Baio JE, Schach D, Bruhn C, Buchholz A, Plass W, Walleck S, Glaser T, Siemeling U (2012) ChemPlusChem 77(10):889–897
Katoh K, Isshiki H, Komeda T, Yamashita M (2011) Coord Chem Rev 255(17–18):2124–2148
Katoh K, Umetsu K, Breedlove Brian K, Yamashita M (2012) Sci China Chem 55(6):918–925
Ganivet CR, Ballesteros B, de la Torre G, Clemente-Juan JM, Coronado E, Torres T (2013) Chem Eur J 19(4):1457–1465
Gonidec M, Luis F, Vílchez À, Esquena J, Amabilino DB, Veciana J (2010) Angew Chem Int Ed 49(9):1623–1626
Cao W, Gao C, Zhang Y, Qi D, Liu T, Wang K, Duan C, Gao S, Jiang J (2015) Chem Sci 6(10):5947–5954
Wang H, Wang K, Tao J, Jiang J (2012) Chem Commun 48(24):2973–2975
Ishikawa N, Otsuka S, Kaizu Y (2005) Angew Chem Int Ed 44(5):731–733
Katoh K, Kajiwara T, Nakano M, Nakazawa Y, Wernsdorfer W, Ishikawa N, Breedlove BK, Yamashita M (2011) Chem Eur J 17(1):117–122
Katoh K, Asano R, Miura A, Horii Y, Morita T, Breedlove BK, Yamashita M (2014) Dalton Trans 43(21):7716–7725
Sakaue S, Fuyuhiro A, Fukuda T, Ishikawa N (2012) Chem Commun 48(43):5337–5339
Kan J, Wang H, Sun W, Cao W, Tao J, Jiang J (2013) Inorg Chem 52(15):8505–8510
Cao W, Wang H, Shang H, Jiang J (2013) Zhongguo Xitu Xuebao 31(5):513–521 (in Chinese)
Wang H, Qian K, Wang K, Bian Y, Jiang J, Gao S (2011) Chem Commun 47(34):9624
Wang H, Liu T, Wang K, Duan C, Jiang J (2012) Chem Eur J 18(25):7691–7694
Fukuda T, Kuroda W, Ishikawa N (2011) Chem Commun 47(42):11686–11688
Fukuda T, Matsumura K, Ishikawa N (2013) J Phys Chem A 117(40):10447–10454
Shang H, Zeng S, Wang H, Dou J, Jiang J (2015) Sci Rep 5:8838
Katoh K, Horii Y, Yasuda N, Wernsdorfer W, Toriumi K, Breedlove BK, Yamashita M (2012) Dalton Trans 41(44):13582–13600
Horii Y, Katoh K, Yasuda N, Breedlove BK, Yamashita M (2015) Inorg Chem 54(7):3297–3305
Wang K, Qi D, Wang H, Cao W, Li W, Liu T, Duan C, Jiang J (2013) Chem Eur J 19(34):11162–11166
Morita T, Katoh K, Breedlove BK, Yamashita M (2013) Inorg Chem 52(23):13555–13561
Blagg RJ, Ungur L, Tuna F, Speak J, Comar P, Collison D, Wernsdorfer W, McInnes EJL, Chibotaru LF, Winpenny REP (2013) Nat Chem 5(8):673–678
Auwaerter W, Ecija D, Klappenberger F, Barth JV (2015) Nat Chem 7(2):105–120
Katoh K, Isshiki H, Komeda T, Yamashita M (2012) Chem Asian J 7(6):1154–1169
Gottfried JM (2015) Surf Sci Rep 70(3):259–379
Komeda T, Isshiki H, Liu J, Zhang Y, Lorente N, Katoh K, Breedlove BK, Yamashita M (2011) Nat Commun 2:217
Robles R, Lorente N, Isshiki H, Liu J, Katoh K, Breedlove BK, Yamashita M, Komeda T (2012) Nano Lett 12(7):3609–3612
Komeda T, Isshiki H, Liu J, Katoh K, Shirakata M, Breedlove BK, Yamashita M (2013) ACS Nano 7(2):1092–1099
Komeda T, Isshiki H, Liu J, Katoh K, Yamashita M (2014) ACS Nano 8(5):4866–4875
Vincent R, Klyatskaya S, Ruben M, Wernsdorfer W, Balestro F (2012) Nature 488(7411):357–360
Thiele S, Balestro F, Ballou R, Klyatskaya S, Ruben M, Wernsdorfer W (2014) Science 344(6188):1135–1138
Stepanow S, Honolka J, Gambardella P, Vitali L, Abdurakhmanova N, Tseng T, Rauschenbach S, Tait SL, Sessi V, Klyatskaya S, Ruben M, Kern K (2010) J Am Chem Soc 132(34):11900–11901
Margheriti L, Chiappe D, Mannini M, Car P, Sainctavit P, Arrio M, de Mongeot FB, Cezar JC, Piras FM, Magnani A, Otero E, Caneschi A, Sessoli R (2010) Adv Mater 22(48):5488–5493
Mannini M, Bertani F, Tudisco C, Malavolti L, Poggini L, Misztal K, Menozzi D, Motta A, Otero E, Ohresser P, Sainctavit P, Condorelli GG, Dalcanale E, Sessoli R (2014) Nat Commun 5:4582
Malavolti L, Mannini M, Car P, Campo G, Pineider F, Sessoli R (2013) J Mater Chem C 1(16):2935–2942
Candini A, Klyatskaya S, Ruben M, Wernsdorfer W, Affronte M (2011) Nano Lett 11(7):2634–2639
Lopes M, Candini A, Urdampilleta M, Reserbat-Plantey A, Bellini V, Klyatskaya S, Marty L, Ruben M, Affronte M, Wernsdorfer W, Bendiab N (2010) ACS Nano 4(12):7531–7537
Wang H, Qian K, Qi D, Cao W, Wang K, Gao S, Jiang J (2014) Chem Sci 5(8):3214–3320
Gonidec M, Biagi R, Corradini V, Moro F, De Renzi V, Del Pennino U, Summa D, Muccioli L, Zannoni C, Amabilino DB, Veciana J (2011) J Am Chem Soc 133(17):6603–6612
Klar D, Candini A, Joly L, Klyatskaya S, Krumme B, Ohresser P, Kappler J, Ruben M, Wende H (2014) Dalton Trans 43(28):10686–10689
Kyatskaya S, Mascarós JRG, Bogani L, Hennrich F, Kappes M, Wernsdorfer W, Ruben M (2009) J Am Chem Soc 131(42):15143–15151
Ganzhorn M, Klyatskaya S, Ruben M, Wernsdorfer W (2013) ACS Nano 7(7):6225–6236
Krull C, Balashov T, Kavich JJ, Mugarza A, Miedema PS, Thakur PK, Sessi V, Klyatskaya S, Ruben M, Stepanow S, Gambardella P, Lodi Rizzini A (2011) Phys Rev Lett 107(17):177205
Lodi Rizzini A, Krull C, Balashov T, Mugarza A, Nistor C, Yakhou F, Sessi V, Klyatskaya S, Ruben M, Stepanow S, Gambardella P (2012) Nano Lett 12(11):5703–5707
Malavolti L, Poggini L, Margheriti L, Chiappe D, Graziosi P, Cortigiani B, Lanzilotto V, de Mongeot FB, Ohresser P, Otero E, Choueikani F, Sainctavit P, Bergenti I, Dediu VA, Mannini M, Sessoli R (2013) Chem Commun 49(98):11506–11508
Acknowledgement
Financial support from the Natural Science Foundation of China, National Key Basic Research Program of China (Grant Nos. 2012CB224801 and 2013CB933400), Beijing Natural Science Foundation, and Fundamental Research Funds for the Central Universities is gratefully acknowledged.
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Bian, Y., Jiang, J. (2015). Recent Advances in Phthalocyanine-Based Functional Molecular Materials. In: Mingos, D. (eds) 50 Years of Structure and Bonding – The Anniversary Volume. Structure and Bonding, vol 172. Springer, Cham. https://doi.org/10.1007/430_2015_194
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