Twists and Turns Around a Square: The Many Faces of Squaraine Chemistry

Luca Beverina; Mauro Sassi

doi:10.1055/s-0033-1340482

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(4): 477-490
DOI: 10.1055/s-0033-1340482

account

Twists and Turns Around a Square: The Many Faces of Squaraine Chemistry

Luca Beverina*

University of Milano-Bicocca, Department of Materials Science and INSTM, Via R. Cozzi 55, 20125 Milano, Italy Fax: +39(02)64485400 eMail: luca.beverina@unimib.it

,

Mauro Sassi

University of Milano-Bicocca, Department of Materials Science and INSTM, Via R. Cozzi 55, 20125 Milano, Italy Fax: +39(02)64485400 eMail: luca.beverina@unimib.it

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Abstract

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Dedicated to Professor Giorgio A. Pagani on the occasion of the 50^th anniversary of his graduation

Abstract

The purpose of this account is to give an overview of the wide variety of available structures that share the common name ‘squaraines’, with particular attention to the results achieved by our group in the last ten years. The first section of the report is an introduction and a description of the motivation for our interest in squaraine compounds. The second section includes a survey of the history of squaraines in the scientific literature, and the third section contains a general description of their synthesis and reactivity, together with reports on our direct experiences of their use in materials science, with a focus on squaraines in third-generation photovoltaics, nonlinear optics, and photodynamic therapy. In all of the cases, we highlight the establishment of structure–property relationships directed at the design of materials with improved properties.

1 Introduction and Motivation

2 Squaraines in the Scientific Literature

3 Synthesis of Squaraine Compounds

3.1 Symmetric Derivatives

3.2 Nonsymmetric Derivatives

3.3 Bis-squaraines

3.4 Core-Substituted Squaraines

3.5 Squaraines That We Have Not (Yet) Tried To Make

4 Conclusion

Key words

squaraines - materials science - conjugation - cyanines - heterocycles

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Referenzen

References
1 Sreejith S, Carol P, Chithra P, Ajayaghosh A. J. Mater. Chem. 2008; 18: 264
2 Ajayaghosh A. Acc. Chem. Res. 2005; 38: 449
3 Hu L, Yan Z, Xu H. RSC Adv. 2013; 3: 7667
4 Beverina L, Salice P. Eur. J. Org. Chem. 2010; 1207
5 Treibs A, Jacob K. Angew. Chem. Int. Ed. Engl. 1965; 4: 694
6 Treibs A, Jacob K. Justus Liebigs Ann. Chem. 1968; 712: 123
7 Treibs A, Jacob K. Justus Liebigs Ann. Chem. 1966; 699: 153
8 Bigelow RW, Freund H.-J. Chem. Phys. 1986; 107: 159
9 Markova LI, Terpetschnig EA, Patsenker LD. Dyes Pigm. 2013; 99: 561
10 Salice P, Arnbjerg J, Pedersen BW, Toftegaard R, Beverina L, Pagani GA, Ogilby PR. J. Phys. Chem. A 2010; 114: 2518
11 Law KY. Chem. Rev. 1993; 93: 449
12 Law KY. J. Phys. Chem. 1987; 91: 5184
13 Law KY. J. Phys. Chem. 1995; 99: 9818
14 Law KY, Bailey FC. J. Org. Chem. 1992; 57: 3278
15 Law KY. Can. J. Chem. 1986; 64: 2267
16 Chen C.-T, Marder SR, Cheng L.-T. J. Am. Chem. Soc. 1994; 116: 3117
17 Ashwell GJ, Roberts MP, Rees ND, Bahra GS, Brown CR. Langmuir 1998; 14: 5279
18 Ashwell GJ, Bahra GS, Brown CR, Hamilton DG, Kennard CH. L, Lynch DE. J. Mater. Chem. 1996; 6: 23
19 Dirk CW, Herndon WC, Cervantes-Lee F, Selnau H, Martinez S, Kalamegham P, Tan A, Campos G, Velez M. J. Am. Chem. Soc. 1995; 117: 2214
20 Meyers F, Chen C.-T, Marder SR, Brédas J.-L, Meyers F. Chem. Eur. J. 1997; 3: 530
21 Chen C.-T, Marder SR, Cheng L.-T. J. Chem. Soc., Chem. Commun. 1994; 259
22 Pawlicki M, Collins HA, Denning RG, Anderson HL. Angew. Chem. Int. Ed. 2009; 48: 3244
23 Wei G, Wang S, Sun K, Thompson ME, Forrest SR. Adv. Energy Mater. 2011; 1: 184
24 Wang S, Hall L, Diev VV, Haiges R, Wei G, Xiao X, Djurovich PI, Forrest SR, Thompson ME. Chem. Mater. 2011; 23: 4789
25 Silvestri F, Irwin MD, Beverina L, Facchetti A, Pagani GA, Marks TJ. J. Am. Chem. Soc. 2008; 130: 17640
26 Tian M, Furuki M, Iwasa I, Sato Y, Pu LS, Tatsuura S. J. Phys. Chem. B 2002; 106: 4370
27 Arunkumar E, Ajayaghosh A, Daub J. J. Am. Chem. Soc. 2005; 127: 3156
28 Shafeekh KM, Rahim MK. A, Basheer MC, Suresh CH, Das S. Dyes Pigm. 2013; 96: 714
29 Lee Y.-D, Lim C.-K, Kim S, Kwon IC, Kim J. Adv. Funct. Mater. 2010; 20: 2786
30 Sreejith S, Divya KP, Ajayaghosh A. Angew. Chem. Int. Ed. 2008; 47: 7883
31 Mayerhöffer U, Fimmel B, Würthner F. Angew. Chem. Int. Ed. 2011; 50: 1
32 Ramaiah D, Eckert I, Arun KT, Weidenfeller L, Epe B. Photochem. Photobiol. 2004; 79: 99
33 Gayathri Devi D, Cibin TR, Ramaiah D, Abraham A. J. Photochem. Photobiol., B 2008; 92: 153
34 Avirah RR, Jayaram DT, Adarsh N, Ramaiah D. Org. Biomol. Chem. 2012; 10: 911
35 Stender B, Völker SF, Lambert C, Pflaum J. Adv. Mater. (Weinheim, Ger.) 2013; 25: 2943
36 Smits EC. P, Setayesh S, Anthopoulos TD, Buechel M, Nijssen W, Coehoorn R, Blom PW. M, de Boer B, de Leeuw DM. Adv. Mater. (Weinheim, Ger.) 2007; 19: 734
37 Arunkumar E, Forbes CC, Noll BC, Smith BD. J. Am. Chem. Soc. 2005; 127: 3288
38 Johnson JR, Fu N, Arunkumar E, Leevy WM, Gammon ST, Piwnica-Worms D, Smith BD. Angew. Chem. Int. Ed. 2007; 46: 5528
39 Collins CG, Baumes JM, Smith BD. Chem. Commun. 2011; 47: 12352
40 Peck EM, Collins CG, Smith BD. Org. Lett. 2013; 15: 2762
41 Sassi M, Crippa M, Ruffo R, Turrisi R, Drees M, Pandey UK, Termine R, Golemme A, Facchetti A, Beverina L. J. Mater. Chem. A 2013; 1: 2631
42 Beverina L, Drees M, Facchetti A, Salamone M, Ruffo R, Pagani GA. Eur. J. Org. Chem. 2011; 5555
43 Abbotto A, Beverina L, Bozio R, Facchetti A, Ferrante C, Pagani GA, Pedron D, Signorini R. Chem. Commun. 2003; 2144
44 Abbotto A, Beverina L, Bozio R, Facchetti A, Ferrante C, Pagani GA, Pedron D, Signorini R. Org. Lett. 2002; 4: 1495
45 Beverina L, Fu J, Leclercq A, Zojer E, Pacher P, Barlow S, Van Stryland EW, Hagan DJ, Brédas J.-L, Marder SR. J. Am. Chem. Soc. 2005; 127: 7282
46 Beverina L, Abbotto A, Landenna M, Cerminara M, Tubino R, Meinardi F, Bradamante S, Pagani GA. Org. Lett. 2005; 7: 4257
47 Chung S.-J, Zheng S, Odani T, Beverina L, Fu J, Padilha LA, Biesso A, Hales JM, Zhan X, Schmidt K, Ye A, Zojer E, Barlow S, Hagan DJ, Van Stryland EW, Yi Y, Shuai Z, Pagani GA, Brédas J.-L, Perry JW, Marder SR. J. Am. Chem. Soc. 2006; 128: 14444
48 Beverina L, Ruffo R, Patriarca G, De Angelis F, Roberto D, Righetto S, Ugo R, Pagani GA. J. Mater. Chem. 2009; 19: 8190
49 Ronchi E, Ruffo R, Rizzato S, Albinati A, Beverina L, Pagani GA. Org. Lett. 2011; 13: 3166
50 Avirah RR, Jyothish K, Suresh CH, Suresh E, Ramaiah D. Chem. Commun. 2011; 47: 12822
51 Jyothish K, Avirah RR, Ramaiah D. Org. Lett. 2006; 8: 111
52 Jisha VS, Arun KT, Hariharan M, Ramaiah D. J. Am. Chem. Soc. 2006; 128: 6024
53 Arunkumar E, Sudeep PK, Kamat PV, Noll BC, Smith BD. New J. Chem. 2007; 31: 677
54 Jyothish K, Arun KT, Ramaiah D. Org. Lett. 2004; 6: 3965
55 Ramaiah D, Joy A, Chandrasekhar N, Eldho NV, Das S, George MV. Photochem. Photobiol. 1997; 65: 783
56 Ramaiah D, Eckert I, Arun KT, Weidenfeller L, Epe B. Photochem. Photobiol. 2002; 76: 672
57 Bonnett R. Chemical Aspects of Photodynamic Therapy . Gordon and Breach Science; Amsterdam: 2000
58 Beverina L, Crippa M, Landenna M, Ruffo R, Salice P, Silvestri F, Versari S, Villa A, Ciaffoni L, Collini E, Ferrante C, Bradamante S, Mari CM, Bozio R, Pagani GA. J. Am. Chem. Soc. 2008; 130: 1894
59 Rapozzi V, Beverina L, Salice P, Pagani GA, Camerin M, Xodo LE. J. Med. Chem. 2010; 53: 2188
60 Beverina L, Crippa M, Salice P, Ruffo R, Ferrante C, Fortunati I, Signorini R, Mari CM, Bozio R, Facchetti A, Pagani GA. Chem. Mater. 2008; 20: 3242
61 Binda M, Agostinelli T, Caironi M, Natali D, Sampietro M, Beverina L, Ruffo R, Silvestri F. Org. Electron. 2009; 10: 1314
62 Silvestri F, López-Duarte I, Seitz W, Beverina L, Martínez-Díaz MV, Marks TJ, Guldi DM, Pagani GA, Torres T. Chem. Commun. 2009; 4500
63 Bagnis D, Beverina L, Huang H, Silvestri F, Yao Y, Yan H, Pagani GA, Marks TJ, Facchetti A. J. Am. Chem. Soc. 2010; 132: 4074
64 Binda M, Iacchetti A, Natali D, Beverina L, Sassi M, Sampietro M. Appl. Phys. Lett. 2011; 98: 073303
65 Iacchetti A, Natali D, Binda M, Beverina L, Sampietro M. Appl. Phys. Lett. 2012; 101: 103307
66 Keil D, Hartmann H. Dyes Pigm. 2001; 49: 161
67 Beverina L, Pagani GA. Acc. Chem. Res. 2013; DOI 10.1021/ar4000967
68 Gerold J, Holzenkamp U, Meier H. Eur. J. Org. Chem. 2001; 2757
69 Nakazumi H, Ohta T, Etoh H, Uno T, Colyer CL, Hyodo Y, Yagi S. Synth. Met. 2005; 153: 33
70 Yagi S, Ohta T, Akagi N, Nakazumi H. Dyes Pigm. 2008; 77: 525
71 Tatarets A, Fedyunyaeva I, Terpetschnig E, Patsenker L. Dyes Pigm. 2005; 64: 125
72 Beverina L, Ruffo R, Mari CM, Pagani GA, Sassi M, De Angelis F, Fantacci S, Yum J.-H, Grätzel M, Nazeeruddin MK. ChemSusChem 2009; 2: 621
73 Mayerhöffer U, Deing K, Gruss K, Braunschweig H, Meerholz K, Würthner F. Angew. Chem. Int. Ed. 2009; 48: 8776
74 Deing KC, Mayerhöffer U, Würthner F, Meerholz K. Phys. Chem. Chem. Phys. 2012; 14: 8328
75 Mayerhöffer U, Würthner F. Angew. Chem. Int. Ed. 2012; 51: 5615
76 Mayerhöffer U, Gsänger M, Stolte M, Fimmel B, Würthner F. Chem. Eur. J. 2012; 19: 218
77 Beverina L, Ruffo R, Salamone MM, Ronchi E, Binda M, Natali D, Sampietro M. J. Mater. Chem. 2012; 22: 6704
78 Ziegenbein W, Sprenger HE. Angew. Chem. 1966; 78: 937
79 Storer RI, Aciro C, Jones LH. Chem. Soc. Rev. 2011; 40: 2330
80 Rostami A, Colin A, Li XY, Chudzinski MG, Lough AJ, Taylor MS. J. Org. Chem. 2010; 75: 3983
81 Nagai A, Chen X, Feng X, Ding X, Guo Z, Jiang D. Angew. Chem. Int. Ed. 2013; 52: 3770
82 Busschaert N, Kirby IL, Young S, Coles SJ, Horton PN, Light ME, Gale PA. Angew. Chem. Int. Ed. 2012; 51: 4426
83 Alemán J, Parra A, Jiang H, Jørgensen KA. Chem. Eur. J. 2011; 17: 6890
84 Baumes JM, Gassensmith JJ, Giblin J, Lee J.-J, White AG, Culligan WJ, Leevy WM, Kuno M, Smith BD. Nat. Chem. 2010; 2: 1025
85 Lee J.-J, Baumes JM, Connell RD, Oliver AG, Smith BD. Chem. Commun. 2011; 47: 7188
86 Yang S, You J, Lan J, Gao G. J. Am. Chem. Soc. 2012; 134: 11868
87 Santos PF, Reis LV, Almeida P, Serrano JP, Oliveira AS, Ferreira LF. V. J. Photochem. Photobiol., A 2004; 163: 267
88 Santos PF, Reis LV, Duarte I, Serrano JP, Almeida P, Oliveira AS, Ferreira LF. V. Helv. Chim. Acta 2005; 88: 1135
89 Xu Y, Li Z, Malkovskiy A, Sun S, Pang Y. J. Phys. Chem. B 2010; 114: 8574
90 Xu Y, Li B, Li W, Zhao J, Sun S, Pang Y. Chem. Commun. 2013; 49: 4764
91 Nakazumi H, Natsukawa K, Nakai K, Isagawa K. Angew. Chem. Int. Ed. Engl. 1994; 33: 1001
92 Basheer MC, Alex S, Thomas KG, Suresh CH, Das S. Tetrahedron 2006; 62: 605
93 Havinga EE, Hoeve W, Wynberg H. Polym. Bull. (Heidelberg, Ger.) 1992; 29: 119
94 Chenthamarakshan CR, Ajayaghosh A. Chem. Mater. 1998; 10: 1657
95 Chenthamarakshan CR, Ajayaghosh A. Tetrahedron Lett. 1998; 39: 1795
96 Eldo J, Ajayaghosh A. Chem. Mater. 2002; 14: 410
97 Chenthamarakshan CR, Eldo J, Ajayaghosh A. Macromolecules 1999; 32: 5846
98 Shi Q, Chen W.-Q, Xiang J, Duan X.-M, Zhan X. Macromolecules 2011; 44: 3759
99 Völker SF, Lambert C. Chem. Mater. 2012; 24: 2541
100 Völker SF, Uemura S, Limpinsel M, Mingebach M, Deibel C, Dyakonov V, Lambert C. Macromol. Chem. Phys. 2010; 211: 1098
101 Maeda T, Tsukamoto T, Seto A, Yagi S, Nakazumi H. Macromol. Chem. Phys. 2012; 213: 2590