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DOI: 10.1055/s-0036-1588685
Donor–Acceptor Molecular Triangles
Publication History
Received: 01 November 2016
Accepted after revision: 13 December 2016
Publication Date:
11 January 2017 (online)
Dedicated to Professor Paul Knochel on the occasion of his presidency at the 51st Bürgenstock Conference
Abstract
The synthesis and optoelectronic properties of five donor–acceptor molecules, featuring an electron-acceptor unit made of six fused benzenoid rings that resembles an equilateral triangle, are described. These molecular ‘triangles’ were synthesized in eight steps from simple building blocks such that the electron-donor substituents could be installed in the last step by means of the Suzuki cross-coupling reaction. All molecules absorb and emit visible light in the region of around 450–650 and 550–850 nm, respectively, exhibit solvatochromism, and possess up to four redox states.
Key words
donor–acceptor molecules - fluorescence - redox properties - solvatochromism - trianguleneSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588685.
- Supporting Information
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Primary Data
- Primary data for this article are available online at http://www.thieme-connect.com/products/ejournals/journal/10.1055/s-00000084 and can be cited using the following DOI: 10.4125/pd0086th.
- Primary Data
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References
- 1 New address: T. Šolomek, Department of Chemistry and Argonne-Northwestern Solar Energy Research Center, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208-3113, USA.
- 2a Pashaei B, Shahroosvand H, Grätzel M, Nazeeruddin MK. Chem. Rev. 2016; 116: 9485
- 2b Nielsen CB, Holliday S, Chen H.-Y, Cryer SJ, McCulloch I. Acc. Chem. Res. 2015; 48: 2803
- 2c Urbani M, Grätzel M, Nazeeruddin MK, Torres T. Chem. Rev. 2014; 114: 12330
- 2d Frischmann PD, Mahata K, Würthner F. Chem. Soc. Rev. 2013; 42: 1847
- 2e Chen X, Li C, Grätzel M, Kostecki R, Mao SS. Chem. Soc. Rev. 2012; 41: 7909
- 3 Schwoerer M, Wolf HC. Organic Molecular Solids . Wiley-VCH; Weinheim: 2007
- 4a Sun M, Müllen K, Yin M. Chem. Soc. Rev. 2016; 45: 1513
- 4b Lavis LD, Raines RT. ACS Chem. Biol. 2008; 3: 142
- 5a The Porphyrin Handbook . Vols. 15–20. Kadish KM, Smith KM, Guilard R. Academic Press; San Diego: 2003
- 5b de la Torre D, Nicolau M, Torres T In Supramolecular Photosensitive and Electroactive Materials . Nalwa HS. Academic Press; New York: 2001: 1-111
- 6a Würthner F, Saha-Möller CR, Fimmel B, Ogi S, Leowanawat P, Schmidt D. Chem. Rev. 2016; 116: 962
- 6b Görl D, Zhang X, Würthner F. Angew. Chem. Int. Ed. 2012; 51: 6328
- 6c Zhan X, Facchetti A, Barlow S, Marks TJ, Ratner MA, Wasielewski MR, Marder SR. Adv. Mater. 2011; 23: 268
- 6d Safont-Sempere MM, Fernández G, Würthner F. Chem. Rev. 2011; 111: 5784
- 7 Fullerenes: Principles and Applications . Langa F, Nierengarten J.-F. The Royal Society of Chemistry; Cambridge: 2007
- 8 Clar E, Stewart DG. J. Am. Chem. Soc. 1953; 75: 2667
- 9a Inoue J, Fukui K, Kubo T, Nakazawa S, Sato K, Shiomi D, Morita Y, Yamamoto K, Takui T, Nakasuji K. J. Am. Chem. Soc. 2001; 123: 12702
- 9b Allinson G, Bushby RJ, Paillaud J.-L, Thornton-Pett M. J. Chem. Soc., Perkin Trans. 1 1995; 385
- 10a Ueda A, Wasa H, Nishida S, Kanzaki Y, Sato K, Takui T, Morita Y. Chem. Asian J. 2013; 8: 2057
- 10b Ueda A, Wasa H, Nishida S, Kanzaki Y, Sato K, Shiomi D, Takui T, Morita Y. Chem. Eur. J. 2012; 18: 16272
- 10c Morita Y, Nishida S, Murata T, Moriguchi M, Ueda A, Satoh M, Arifuku K, Sato K, Takui T. Nat. Mater. 2011; 10: 947
- 11a Wallabregue A, Moreau D, Sherin P, Moneva Lorente P, Jarolímová Z, Bakker E, Vauthey E, Gruenberg J, Lacour J. J. Am. Chem. Soc. 2016; 138: 1752
- 11b Adam C, Wallabregue A, Li H, Gouin J, Vanel R, Grass S, Bosson J, Bouffier L, Lacour J, Sojic N. Chem. Eur. J. 2015; 21: 19243
- 11c Bosson J, Gouin J, Lacour J. Chem. Soc. Rev. 2014; 43: 2824
- 11d Hamacek J, Besnard C, Mehanna N, Lacour J. Dalton Trans. 2012; 41: 6777
- 11e Nicolas C, Bernardinelli G, Lacour J. J. Phys. Org. Chem. 2010; 23: 1049
- 11f Laursen BW, Krebs FC. Chem. Eur. J. 2001; 7: 1773
- 11g Hellwinkel D, Aulmich G, Melan M. Chem. Ber. 1981; 114: 86
- 12a Hammer N, Schaub TA, Meinhardt U, Kivala M. Chem. Rec. 2015; 15: 1119
- 12b Kivala M, Pisula W, Wang S, Marvinskiy A, Gisselbrecht J.-P, Feng X, Müllen K. Chem. Eur. J. 2013; 19: 8117
- 13 Iwahara H, Kushida T, Yamaguchi S. Chem. Commun. 2016; 52: 1124
- 14 Huang C, Barlow S, Marder SR. J. Org. Chem. 2011; 76: 2386
- 15 Wegner HA, Reisch H, Rauch K, Demeter A, Zachariasse KA, de Meijere A, Scott LT. J. Org. Chem. 2006; 71: 9080
- 16a Hoffmann V, Jenny N, Häussinger D, Neuburger M, Mayor M. Eur. J. Org. Chem. 2016; 2187
- 16b He Y, Johansson M, Sterner O. Synth. Commun. 2004; 32: 4153
- 17 Dalcanale E, Montanari F. J. Org. Chem. 1986; 51: 567
- 18 Compound T2 was crystallized from a solution in CH2Cl2/MeOH (1:1) by slow evaporation of the solvent mixture. Crystallographic parameters: C41H40O3; 0.06 × 0.06 × 0.11 mm; monoclinic, C2/c (No. 15); a = 17.6046(12), b = 15.1726(10), and c = 24.4615(16) Å; α = 90, β = 107.854(2), and γ = 90°; V = 6219.2(7) Å3; Z = 8; T = 123 K; ρcalc = 1.240 g cm–3; μ = 0.595 mm–1. CCDC 1513957 contains the supplementary crystallographic data for this compound. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
- 19 Compound T3 was crystallized from a solution in CH2Cl2/MeCN (1:1) by slow evaporation of the solvent mixture. Crystallographic parameters: [C42H43NO2]·0.5(CH2Cl2); 0.07 × 0.09 × 0.10 mm; orthorhombic, Pnnm (No. 58); a = 14.8990(11), b = 25.4300(19), and c = 9.5165(7) Å; α = 90, β = 90, and γ = 90°; V = 3505.6(5) Å3; Z = 4; T = 123 K; ρcalc = 1.1600 g cm–3; μ = 1.196 mm–1. CCDC 1513958 contains the supplementary crystallographic data for this compound. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
- 20 An Z, Odom SA, Kelley RF, Huang C, Zhang X, Barlow S, Padilha LA, Fu J, Webster S, Hagan DJ, Van Stryland EW, Wasielewski MR, Marder SR. J. Phys. Chem. A 2009; 113: 5585
- 21 Nakazono S, Easwaramoorthi S, Kim D, Shinokubo H, Osuka A. Org. Lett. 2009; 11: 5426
- 22 Dey S, Efimov A, Lemmetyinen H. Eur. J. Org. Chem. 2012; 2367
- 23 Shoer LE, Eaton SW, Margulies EA, Wasielewski MR. J. Phys. Chem. B 2015; 119: 7635
- 24 Hartnett PE, Margulies EA, Matte HS. S. R, Hersam MC, Marks TJ, Wasielewski MR. Chem. Mater. 2016; 28: 3928
- 25 Eaton SW, Shoer LE, Karlen SD, Dyar SM, Margulies EA, Veldkamp BS, Ramanan C, Hartzler DA, Savikhin S, Marks TJ, Wasielewski MR. J. Am. Chem. Soc. 2013; 135: 14701
- 26 Fulmer GR, Miller AJ. M, Sherden NH, Gottlieb HE, Nudelman A, Stoltz BM, Bercaw JE, Goldberg KI. Organometallics 2010; 29: 2176
- 27 Bruker Analytical X-ray Systems, Inc., APEX2, Version 2 User Manual, M86–E01078. Bruker; Madison WI: 2006
- 28 Palatinus L, Chapuis G. J. Appl. Crystallogr. 2007; 40: 786
- 29 Betteridge PW, Carruthers JR, Cooper RI, Prout K, Watkin DJ. J. Appl. Crystallogr. 2003; 36: 1487
- 30a Macrae CF, Bruno IJ, Chisholm JA, Edgington PR, McCabe P, Pidcock E, Rodriguez-Monge L, Taylor R, van de Streek J, Wood PA. J. Appl. Crystallogr. 2008; 41: 466
- 30b Bruno IJ, Cole JC, Edgington PR, Kessler M, Macrae CF, McCabe P, Pearson J, Taylor R. Acta Crystallogr. 2002; 58: 389
- 31 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA. Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision D.01. Gaussian, Inc; Wallingford: 2009