Abstract
Self-assembly has been utilized for the spontaneous formation of nanoarchitectures. Therein, a small change in the molecular structure dramatically alters the resulting macroscopic self-assembly morphologies and the consequent material properties. This macroscopic expression of the small initial difference via self-assembly can be alternatively regarded as precise translation of molecular structural information. In this chapter, we offer a novel molecular recognition concept utilizing self-assembly phenomena. A small difference in guest structures affords distinctly different self-assembly modes of fluorescent (FL) chemosensors and leads to their sensory responses characteristic of the guest structures. Thus, self-assembly has now been utilized as a FL sensory system for molecular recognition, particularly, of biologically important molecules and macromolecules. Through these studies, we wish to demonstrate why the AIE-based recognition is superior to that of unimolecule-based recognition.
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References
Giepmans BNG, Adams SR, Ellisman MH, Tsien RY (2006). Science 312:217
Domaille DW, Que EL, Chang CJ (2008). Nat Chem Biol 4:168
Hargrove AE, Nieto S, Zhang T, Sessler JL, Anslyn EV (2011). Chem Rev 111:6603
MartÃnez-máñez R, Sancenón F (2003). Chem Rev 103:4419
Lakowicz JR (1999) Principles of fluorescence spectroscopy2nd edn. Kluwer Academic/Plenum, New York
Lehn J-M (1995) Supramolecular chemistry: concepts and perspectives. Wiley-VCH, Weinheim
Boyer PD (1998). Angew Chem Int Ed 37:2296
Ngo HT, Liu X, Jolliffe KA (2012). Chem Soc Rev 41:4928
Ojida A, Takashima I, Kohira T, Nonaka H, Hamachi I (2008). J Am Chem Soc 130:12095
Whitesides GM, Mathias JP, Seto CT (1991). Science 254:1312
Zhang S (2003). Nat Biotechnol 21:1171
Hoeben FJM, Jonkheijm P, Meijer EW, Schenning APHJ (2005). Chem Rev 105:1491
Elemans JAAW, van Hameren R, Nolte RJM, Rowan AE (2006). Adv Mater 18:1251
Palmer LC, Stupp SI (2008). Acc Chem Res 41:1674
Frischmann PD, Mahata K, Würthner F (2013). Chem Soc Rev 42:1847
Faul CFJ (2014). Acc Chem Res 47:3428
Babu SS, Praveen VK, Ajayaghosh A (2014). Chem Rev 114:1973
Yagai S, Okamura S, Nakano Y, Yamauchi M, Kishikawa K, Karatsu T, Kitamura A, Ueno A, Kuzuhara D, Yamada H, Seki T, Ito H (2014). Nat Commun 5:4013
Sun Q-F, Iwasa J, Ogawa D, Ishido Y, Sato S, Ozeki T, Sei Y, Yamaguchi K, Fujita M (2010). Science 328:1144
Yagai S, Goto Y, Lin X, Karatsu T, Kitamura A, Kuzuhara D, Yamada H, Kikkawa Y, Saeki A, Seki S (2012). Angew Chem Int Ed 51:6643
Oda R, Huc I, Schmutz M, Candau SJ, MacKintosh FC (1999). Nature 399:566
Noguchi T, Chikara C, Kuroiwa K, Kaneko K, Kimizuka N (2011). Chem Commun 47:6455
Noguchi T, Kimizuka N (2014). Chem Commun 50:599
Ishiba K, Noguchi T, Iguchi H, Morikawa M, Kaneko K, Kimizuka N (2017). Angew Chem Int Ed 56:2974
Noguchi T, Shiraki T, Dawn A, Tsuchiya Y, Lien LTN, Yamamoto T, Shinkai S (2012). Chem Commun 48:8090
Noguchi T, Dawn A, Yoshihara D, Tsuchiya Y, Yamamoto T, Shinkai S (2013). Macromol Rapid Commun 34:779
Noguchi T, Roy B, Yoshihara D, Tsuchiya Y, Yamamoto T, Shinkai S (2014). Chem Eur J 20:13938
Noguchi T, Roy B, Yoshihara D, Tsuchiya Y, Yamamoto T, Shinkai S (2015). Chem Sci 6:3863
Noguchi T, Roy B, Yoshihara D, Sakamoto J, Yamamoto T, Shinkai S (2016). Angew Chem Int Ed 55:5708
Noguchi T, Roy B, Yoshihara D, Sakamoto J, Yamamoto T, Shinkai S (2017). Angew Chem Int Ed 56:12518
Noguchi T, Yoshihara D, Shinkai S (2017). J Synth Org Chem 75:49
Tong H, Hong Y, Dong Y, Häußler M, Lam JWY, Li Z, Guo Z, Guo Z, Tang BZ (2006). Chem Comm (35):3705
Blondeau P, Segura M, P-Fernandez R, Mendoza J (2007). Chem Soc Rev 36:198
Ikeda T, Hirata O, Takeuchi M, Shinkai S (2006). J Am Chem Soc 128:16008
Tian W-N, Braunstein LD, Pang J, Stuhlmeier KM, Xi Q-C, Tian X, Stanton RC (1998). J Biol Chem 273:10609
Jiang P, Du W, Wang X, Mancuso A, Gao X, Wu M, Yang X (2011). Nat Cell Biol 13:310
Freeman R, Gill R, Shweky I, Kotler M, Banin U, Willner I (2009). Angew Chem Int Ed 48:309
Kasha M, Rawls HR, El-Bayoumi MA (1965). Pure Appl Chem 11:371
Würthner F, Kaiser TE, Saha-Möller CR (2011). Angew Chem Int Ed 50:3376
Babu SS, Prasanthkumar S, Ajayaghosh A (2012). Angew Chem Int Ed 51:1766
Maggini L, Bonifazi D (2012). Chem Soc Rev 41:211
Yoon S-J, Park SY (2011). J Mater Chem 21:8338
Yoon S-J, Chung JW, Gierschner J, Kim KS, Choi M-G, Kim D, Park SY (2010). J Am Chem Soc 132:13675
Ascenso J, Gil VMS (1980). Can J Chem 58:1376
Yoshihara D, Noguchi T, Tsuchiya Y, Roy B, Yamamoto T, Shinkai S (2015). Chem Lett 44:812
Shinkai S, Tsukagoshi K, Ishikawa Y, Kunitake T (1991) J Chem Soc. Chem Commun (15):1039
Fujita N, Shinkai S, James TD (2008). Chem Asian J 3:1076
Li Y, Zhou S (2013). Chem Commun 49:5553
Hirono S, Hayashi C, Igarashi M, Nishimura Y, Toshima K (2010). Angew Chem Int Ed 49:10096
Yoshihara D, Noguchi T, Roy B, Sakamoto J, Yamamoto T, Shinkai S (2016). Chem Lett 45:702
Ko S-O, Schlautman MA, Carraway ER (1998). Environ Sci Technol 32:3542
Peyser YM, Ben-Hur M, Werber MM, Muhlrad A (1996). J Am Chem Soc 35:4409
Nitta R, Okada Y, Hirokawa N (2008). Nat Struct Mol Biol 15:1067
Metzger A, Anslyn EV (1998). Angew Chem Int Ed 37:649
Choudhury SD, Mohanty J, Pal H, Bhasikuttan AC (2010). J Am Chem Soc 132:1395
Capila I, Linhardt RJ (2002). Angew Chem Int Ed 41:390
Pettersson T, Fröseth B, Riska H, Klockars M (1988). Chest 94:1037
Hillerdal G, Lindqvist U, Engström-Laurent A (1991). Cancer 67:2410
Lokeshwar VB, Öbek C, Soloway MS, Block NL (1997). Cancer Res 57:773
Wong VS, Hughes V, Trull A, Wight DGD, Petrik J, Alexander GJM (1998). J Viral Hepat 5:187
Fujimoto N, Gemba K, Asano M, Fuchimoto Y, Wada S, Ono K, Ozaki S, Kishimoto T (2013). Respir Investig 51:92
Salanti A, Clausen TM, Agerbæk MØ, Nakouzi NA, Dahlbäck M, Oo HZ, Lee S, Gustavsson T, Rich JR, Hedberg BJ, Mao Y, Barington L, Pereira MA, LoBello J, Endo M, Fazli L, Soden J, Wang CK, Sander AF, Dagil R, Thrane S, Holst PJ, Meng L, Favero F, Weiss GJ, Nielsen MA, Freeth J, TO N, Zaia J, Tran NL, Trent J, Babcook JS, Theander TG, Sorensen PH, Daugaard M (2015). Cancer Cell 28:1
Hunter CA, Anderson HL (2009). Angew Chem Int Ed 48:7488
Montalvo GL, Zhang Y, Young TM, Costanzo MJ, Freeman KB, Wang J, Clements DJ, Magavern E, Kavash RW, Scott RW, Liu D, DeGrado WF (2014). ACS Chem Biol 9:967
Bromfield SM, Posocco P, Chan CW, Calderon M, Guimond SE, Turnbull JE, Pricl S, Smith DK (2014). Chem Sci 5:1484
Bromfield SM, Smith DK (2015). J Am Chem Soc 137:10056
Wright AT, Zhong Z, Anslyn EV (2005). Angew Chem Int Ed 44:5679
Sun W, Bandmann H, Schrader T (2007). Chem Eur J 13:7701
Yeung MC-L, Yam VW-W (2011). Chem Eur J 17:11987
Dai Q, Liu W, Zhuang X, Wu J, Zhang H, Wang P (2011). Anal Chem 83:6559
Bromfield SM, Barnard A, Posocco P, Fermeglia M, Pricl S, Smith DK (2013). J Am Chem Soc 135:2911
Bromfield SM, Wilde E, Smith DK (2013). Chem Soc Rev 42:9184
Wang M, Zhang D, Zhang G, Zhu D (2008). Chem Comm (37):4469
Gu X, Zhang G, Zhang D (2012). Analyst 137:365
Kwok RTK, Geng J, Lam JWY, Zhao E, Wang G, Zhan R, Liu B, Tang BZ (2014). J Mater Chem B 2:4134
Ding Y, Shi L, Wei H (2015). Chem Sci 6:6361
Pivovarenko VG, Vadzyuk OB, Kosterin SO (2006). J Fluoresc 16:9
Tang L, Park J, Kim HJ, Kim Y, Kim SJ, Chin J, Kim KM (2008). J Am Chem Soc 130:12606
Acknowledgments
This work was supported by the Ministry of Education, Culture, Sports, Science and Technology of Japan, Grant-in-Aid for Scientific Research (C) (Grant Number 17K05848) and for Young Scientists B (Grant Numbers JP25810051 and JP16K17937).
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Noguchi, T., Yoshihara, D., Shinkai, S. (2019). Applications of AIE to Molecular Recognition: Why Is It Superior to Unimolecular Recognition?. In: Tang, Y., Tang, B. (eds) Principles and Applications of Aggregation-Induced Emission. Springer, Cham. https://doi.org/10.1007/978-3-319-99037-8_8
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