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Pure Appl. Chem., 2006, Vol. 78, No. 12, pp. 2341-2349

http://dx.doi.org/10.1351/pac200678122341

Bay-substituted perylene bisimides: Twisted fluorophores for supramolecular chemistry

Frank Würthner

Universität Würzburg, Institut für Organische Chemie, Am Hubland,97074 Würzburg, Germany

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  • Yuan Chunxue, Saito Shohei, Camacho Cristopher, Kowalczyk Tim, Irle Stephan, Yamaguchi Shigehiro: Hybridization of a Flexible Cyclooctatetraene Core and Rigid Aceneimide Wings for Multiluminescent Flapping π Systems. Chem. Eur. J. 2014, 20, 2193. <http://dx.doi.org/10.1002/chem.201303955>
  • Mishra Ruchika, Lim Jong Min, Son Minjung, Panini Piyush, Kim Dongho, Sankar Jeyaraman: Tuning the Electronic Nature of Mono-Bay Alkynyl-Phenyl-Substituted Perylene Bisimides: Synthesis, Structure and Photophysical Properties. Chem. Eur. J. 2014, n/a. <http://dx.doi.org/10.1002/chem.201400099>
  • Roznyatovskiy Vladimir V., Gardner Daniel M., Eaton Samuel W., Wasielewski Michael R.: Radical Anions of Trifluoromethylated Perylene and Naphthalene Imide and Diimide Electron Acceptors. Org. Lett. 2014, 16, 696. <http://dx.doi.org/10.1021/ol403736m>
  • Jiménez Ángel J., Lin Mei-Jin, Burschka Christian, Becker Johannes, Settels Volker, Engels Bernd, Würthner Frank: Structure–property relationships for 1,7-diphenoxy-perylene bisimides in solution and in the solid state. Chem. Sci. 2014, 5, 608. <http://dx.doi.org/10.1039/c3sc52344f>
  • Heek Timm, Würthner Frank, Haag Rainer: Synthesis and Optical Properties of Water-Soluble Polyglycerol-Dendronized Rylene Bisimide Dyes. Chem. Eur. J. 2013, 19, 10911. <http://dx.doi.org/10.1002/chem.201300556>
  • Geib Sonja, Martens Susanne C., Märken Michaela, Rybina Arina, Wadepohl Hubert, Gade Lutz H.: Tuning Redox Chemistry and Photophysics in Core-Substituted Tetraazaperopyrenes (TAPPs). Chem. Eur. J. 2013, 19, 13811. <http://dx.doi.org/10.1002/chem.201301903>
  • Selig Ulrike, Nuernberger Patrick, Dehm Volker, Settels Volker, Gsänger Marcel, Engels Bernd, Würthner Frank, Brixner Tobias: Similarities and Differences in the Optical Response of Perylene-Based Hetero-Bichromophores and Their Monomeric Units. ChemPhysChem 2013, 14, 1413. <http://dx.doi.org/10.1002/cphc.201300062>
  • Li Chen, Stepanenko Vladimir, Lin Mei-Jin, Hong Wenjing, Würthner Frank, Wandlowski Thomas: Charge transport through perylene bisimide molecular junctions: An electrochemical approach. Phys. Status Solidi B 2013, 250, 2458. <http://dx.doi.org/10.1002/pssb.201350034>
  • Kawasumi Katsuaki, Mochida Kenji, Segawa Yasutomo, Itami Kenichiro: Palladium-catalyzed direct phenylation of perylene: structural and optical properties of 3,4,9-triphenylperylene and 3,4,9,10-tetraphenylperylene. Tetrahedron 2013, 69, 4371. <http://dx.doi.org/10.1016/j.tet.2013.01.037>
  • Heek Timm, Nikolaus Jörg, Schwarzer Roland, Fasting Carlo, Welker Pia, Licha Kai, Herrmann Andreas, Haag Rainer: An Amphiphilic Perylene Imido Diester for Selective Cellular Imaging. Bioconjugate Chem. 2013, 24, 153. <http://dx.doi.org/10.1021/bc3005655>
  • Yuan Chunxue, Saito Shohei, Camacho Cristopher, Irle Stephan, Hisaki Ichiro, Yamaguchi Shigehiro: A π-Conjugated System with Flexibility and Rigidity That Shows Environment-Dependent RGB Luminescence. J. Am. Chem. Soc. 2013, 135, 8842. <http://dx.doi.org/10.1021/ja404198h>
  • Rieth Stephen, Li Zhong, Hinkle Charlotte E., Guzman Carmen X., Lee Jungeun J., Nehme Samer I., Braunschweig Adam B.: Superstructures of Diketopyrrolopyrrole Donors and Perylenediimide Acceptors Formed by Hydrogen-Bonding and π···π Stacking. J. Phys. Chem. C 2013, 117, 11347. <http://dx.doi.org/10.1021/jp400918z>
  • Frischmann Peter D., Würthner Frank: Synthesis of a Non-aggregating Bay-Unsubstituted Perylene Bisimide Dye with Latent Bromo Groups for C–C Cross Coupling. Org. Lett. 2013, 15, 4674. <http://dx.doi.org/10.1021/ol401946g>
  • Lin Mei-Jin, Schulze Marcus, Radacki Krzysztof, Würthner Frank: Transition metal complexes of axially chiral tetrathioether bay-substituted perylene bisimide dyes. Chem. Commun. 2013, 49, 9107. <http://dx.doi.org/10.1039/c3cc45351k>
  • Llansola-Portoles Manuel J., Bergkamp Jesse J., Tomlin John, Moore Thomas A., Kodis Gerdenis, Moore Ana L., Cosa Gonzalo, Palacios Rodrigo E.: Photoinduced Electron Transfer in Perylene-TiO2 Nanoassemblies. Photochem Photobiol 2013, 89, 1375. <http://dx.doi.org/10.1111/php.12108>
  • Yang Si Kyung, Zimmerman Steven C.: Polyglycerol-Dendronized Perylenediimides as Stable, Water-Soluble Fluorophores. Adv. Funct. Mater. 2012, 22, 3023. <http://dx.doi.org/10.1002/adfm.201200004>
  • Li Yongjun, Qing Zhihong, Yu Yanwen, Liu Taifeng, Jiang Runsheng, Li Yuliang: Synthesis and Self-Assembly of Dihydroxyperylene Bisimides for the Tuning of Photophysical Properties. Chem. Asian J. 2012, 7, 1934. <http://dx.doi.org/10.1002/asia.201200243>
  • Xie Zengqi, Stepanenko Vladimir, Radacki Krzysztof, Würthner Frank: Chiral J-Aggregates of Atropo-Enantiomeric Perylene Bisimides and Their Self-Sorting Behavior. Chem. Eur. J. 2012, 18, 7060. <http://dx.doi.org/10.1002/chem.201200089>
  • Lee I-Lin, Li Sie-Rong, Chen Kuan-Fu, Ku Po-Jen, Singh Ashutosh S., Kuo Hui-Tung, Wen Yuh-Sheng, Chu Chi-Wei, Sun Shih-Sheng: Synthesis, Photophysical Properties, and Field-Effect Characteristics of (Ethynylphenyl)benzimidazole-Decorated Anthracene and Perylene Bisimide Derivatives. Eur J Org 2012, 2012, 2906. <http://dx.doi.org/10.1002/ejoc.201200032>
  • Schönamsgruber Jörg, Schade Boris, Kirschbaum Rolf, Li Jing, Bauer Walter, Böttcher Christoph, Drewello Thomas, Hirsch Andreas: Synthesis and Aggregation Properties of Polycationic Perylenetetracarboxylic Acid Diimides. Eur. J. Org. Chem. 2012, 2012, 6179. <http://dx.doi.org/10.1002/ejoc.201201062>
  • Quartarolo Angelo Domenico, Chiodo Sandro Giuseppe, Russo Nino: A TDDFT investigation of bay substituted perylenediimides: Absorption and intersystem crossing. J  Comput Chem 2012, 33, 1091. <http://dx.doi.org/10.1002/jcc.22914>
  • Dolfen Daniel, Schottler Kristina J., Scherf Ullrich: Polyelectrolytes with Main-Chain Perylene Units. Macromol. Rapid Commun. 2012, 33, 1542. <http://dx.doi.org/10.1002/marc.201200206>
  • Diacon Aurel, Mocanu Alexandra, Boscornea Cristian, Hudhomme Piétrick: Monomer type emission of perylenediimide derivatives doped polymer particles. Colloids and Surfaces A: Physicochemical and Engineering Aspects 2012, 407, 9. <http://dx.doi.org/10.1016/j.colsurfa.2012.02.051>
  • Miasojedovas A., Kazlauskas K., Armonaite G., Sivamurugan V., Valiyaveettil S., Grazulevicius J.V., Jursenas S.: Concentration effects on emission of bay-substituted perylene diimide derivatives in a polymer matrix. J Dye Pig 2012, 92, 1285. <http://dx.doi.org/10.1016/j.dyepig.2011.09.017>
  • Chen Yanli, Feng Yajuan, Gao Jian, Bouvet Marcel: Self-assembled aggregates of amphiphilic perylene diimide–based semiconductor molecules: Effect of morphology on conductivity. Journal of Colloid and Interface Science 2012, 368, 387. <http://dx.doi.org/10.1016/j.jcis.2011.10.076>
  • de Miguel Maykel, Álvaro Mercedes, García Hermenegildo, Céspedes-Guirao F. Javier, Fernández-Lázaro Fernando, Sastre-Santos Ángela: Selective photoinduced single or double electron reduction of perylenebisimides. J Photochem Photobiol A Chem 2012, 231, 28. <http://dx.doi.org/10.1016/j.jphotochem.2012.01.008>
  • Oltean Mircea, Calborean Adrian, Mile George, Vidrighin Mihai, Iosin Monica, Leopold Loredana, Maniu Dana, Leopold Nicolae, Chiş Vasile: Absorption spectra of PTCDI: A combined UV–Vis and TD-DFT study. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2012, 97, 703. <http://dx.doi.org/10.1016/j.saa.2012.07.056>
  • Mizoshita Norihiro, Yamanaka Ken-ichi, Hiroto Satoru, Shinokubo Hiroshi, Tani Takao, Inagaki Shinji: Energy and Electron Transfer from Fluorescent Mesostructured Organosilica Framework to Guest Dyes. Langmir 2012, 28, 3987. <http://dx.doi.org/10.1021/la204645k>
  • Sun Yan, Li Zhibo, Wang Zhaohui: Self-assembled monolayer and multilayer films based on l-lysine functionalized perylene bisimide. J Materials Chemistry 2012, 22, 4312. <http://dx.doi.org/10.1039/c1jm14521e>
  • Lin Mei-Jin, Jiménez Ángel J., Burschka Christian, Würthner Frank: Bay-substituted perylene bisimide dye with an undistorted planar scaffold and outstanding solid state fluorescence properties. Chem. Commun. 2012, 48, 12050. <http://dx.doi.org/10.1039/c2cc36719j>
  • Spreitler Florian, Sommer Michael, Thelakkat Mukundan, Köhler Jürgen: Conformational dynamics of di-(perylene bisimide acrylate) and its footprints in steady-state, time-resolved, and fluorescence-correlation spectroscopy. PCCP 2012, 14, 7971. <http://dx.doi.org/10.1039/c2cp40387k>
  • Issac Abey, Hildner Richard, Ernst Dominique, Hippius Catharina, Würthner Frank, Köhler Jürgen: Single molecule studies of calix[4]arene-linked perylene bisimide dimers: relationship between blinking, lifetime and/or spectral fluctuations. Phys. Chem. Chem. Phys. 2012, 14, 10789. <http://dx.doi.org/10.1039/c2cp41250k>
  • Winter Andreas, Hoeppener Stephanie, Newkome George R., Schubert Ulrich S.: Terpyridine-Functionalized Surfaces: Redox-Active, Switchable, and Electroactive Nanoarchitecturesgland. Advanced Materials (Weinheim Germany) 2011, 23, 3484. <http://dx.doi.org/10.1002/adma.201101251>
  • Krause Stefan, Kowerko Danny, Börner Richard, Hübner Christian G., von Borczyskowski Christian: Spectral Diffusion of Single Molecules in a Hierarchical Energy Landscape. Chem Eur J of Chem Phys 2011, 12, 303. <http://dx.doi.org/10.1002/cphc.201000678>
  • Perrin Lara, Hudhomme Piétrick: Synthesis, Electrochemical and Optical Absorption Properties of New Perylene-3,4:9,10-bis(dicarboximide) and Perylene-3,4:9,10-bis(benzimidazole) Derivatives. Eur J Org Chem 2011, 2011, 5427. <http://dx.doi.org/10.1002/ejoc.201100513>
  • Franceschin Marco, Borbone Nicola, Oliviero Giorgia, Casagrande Valentina, Scuotto Maria, Coppola Teresa, Borioni Silvia, Mayol Luciano, Ortaggi Giancarlo, Bianco Armandodoriano: Synthesis of a Dibromoperylene Phosphoramidite Building Block and Its Incorporation at the 5′ End of a G-Quadruplex Forming Oligonucleotide: Spectroscopic Properties and Structural Studies of the Resulting Dibromoperylene Conjugate. Bioconjugate Chem 2011, 22, 1309. <http://dx.doi.org/10.1021/bc100526q>
  • Yang Si Kyung, Shi Xinghua, Park Seongjin, Doganay Sultan, Ha Taekjip, Zimmerman Steven C.: Monovalent, Clickable, Uncharged, Water-Soluble Perylenediimide-Cored Dendrimers for Target-Specific Fluorescent Biolabeling. J Am Chcm Soc 2011, 133, 9964. <http://dx.doi.org/10.1021/ja2009136>
  • Di Motta Simone, Siracusa Melania, Negri Fabrizia: Structural and Thermal Effects on the Charge Transport of Core-Twisted Chlorinated Perylene Bisimide Semiconductors. J Phys Chem C 2011, 115, 20754. <http://dx.doi.org/10.1021/jp207333y>
  • Diacon Aurel, Rusen Edina, Mocanu Alexandra, Hudhomme Piétrick, Cincu Corneliu: Fluorescence Properties of Photonic Crystals Doped with Perylenediimide. Langmiur 2011, 27, 7464. <http://dx.doi.org/10.1021/la200878b>
  • Sun Yan, He Chang, Sun Kai, Li Yan, Dong Huanli, Wang Zhaohui, Li Zhibo: Fine-Tuned Nanostructures Assembled from l-Lysine-Functionalized Perylene Bisimides. Langmir 2011, 27, 11364. <http://dx.doi.org/10.1021/la202107r>
  • Battagliarin Glauco, Li Chen, Enkelmann Volker, Müllen Klaus: 2,5,8,11-Tetraboronic Ester Perylenediimides: A Next Generation Building Block for Dye-Stuff Synthesis. Org Lett 2011, 13, 3012. <http://dx.doi.org/10.1021/ol2008457>
  • Krause Stefan, Aramendia Pedro F., Täuber Daniela, von Borczyskowski Christian: Freezing single molecule dynamics on interfaces and in polymers. Phys Chem Chem Phys 2011, 13, 1754. <http://dx.doi.org/10.1039/c0cp01713b>
  • Seki Tomohiro, Maruya Yukihiro, Nakayama Ken-ichi, Karatsu Takashi, Kitamura Akihide, Yagai Shiki: Solution processable hydrogen-bonded perylene bisimide assemblies organizing into lamellar architectures. Chem Commn 2011, 47, 12447. <http://dx.doi.org/10.1039/c1cc15118e>
  • Ambrosek David, Marciniak Henning, Lochbrunner Stefan, Tatchen Jörg, Li Xue-Qing, Würthner Frank, Kühn Oliver: Photophysical and quantum chemical study on a J-aggregate forming perylene bisimide monomer. PCCP 2011, 13, 17649. <http://dx.doi.org/10.1039/c1cp21624d>
  • Reghu Renji R., Bisoyi Hari Krishna, Grazulevicius Juozas V., Anjukandi Padmesh, Gaidelis Valentas, Jankauskas Vygintas: Air stable electron-transporting and ambipolar bay substituted perylene bisimides. J Mater Chem 2011, 21, 7811. <http://dx.doi.org/10.1039/c1jm11091h>
  • Simonov Sergey, Lemouchi Cyprien, Zorina Leokadiya, Gautier Christelle, Hudhomme Piétrick, Batail Patrick: Amino acid derivatives of perylenediimide and their N–H⋯O peptide bond dipoles-templated solid state assembly into stacks. Biomol Chem 2011, 9, 8096. <http://dx.doi.org/10.1039/c1ob06213a>
  • Shin Man-Sub, Lee Sang-Jin, Chin Sung-Min, Lee Seung-Hee, Pore D.M., Park Yoon-Kook, Lee Sueg-Geun, Hwang Kwang-Jin: Synthesis of Novel Fluorophores Derived from Pyranylidenemalonitrile. Bull Kor Chem Soc 2011, 32, 3152. <http://dx.doi.org/10.5012/bkcs.2011.32.8.3152>
  • Xu Xiao-Hui, Liu Xiao-Yun, Zhuang Qi-Xin, Han Zhe-Wen: Rigid-rod polybenzoxazoles containing perylene bisimide: Synthesis, structures and photophysical properties. J Appl Polym Sci 2010, 116, 455. <http://dx.doi.org/10.1002/app.31485>
  • Pucci Andrea, Donati Filippo, Nazzi Samuele, Barretta Gloria Uccello, Pescitelli Gennaro, Bari Lorenzo Di, Ruggeri Giacomo: Association phenomena of a chiral perylene derivative in solution and in poly(ethylene) dispersion. React & Funct Polym 2010, 70, 951. <http://dx.doi.org/10.1016/j.reactfunctpolym.2010.09.001>
  • Wu Xue, Yin Chuanwei, Shi Zhiqiang, Xu Maoyou, Zhang Jin, Sun Juanjuan: A novel substitution reaction of perylene bisimides with Ph2PLi at the α-position. New J Chem 2010, 34, 61. <http://dx.doi.org/10.1039/b9nj00364a>
  • Queste Mathieu, Cadiou Cyril, Pagoaga Bernard, Giraudet Louis, Hoffmann Norbert: Synthesis and characterization of 1,7-disubstituted and 1,6,7,12-tetrasubstituted perylenetetracarboxy-3,4:9,10-diimide derivatives. New J Chem 2010, 34, 2537. <http://dx.doi.org/10.1039/c0nj00240b>
  • Schnitzler Tobias, Li Chen, Müllen Klaus: Synthesis and Characterization of Pentafluorophenyl-Substituted Perylenebis(dicarboximides). HCA 2009, 92, 2525. <http://dx.doi.org/10.1002/hlca.200900218>
  • Scholz Markus, Schmidt Rüdiger, Krause Stefan, Schöll Achim, Reinert Friedrich, Würthner Frank: Electronic structure of epitaxial thin films of bay-substituted perylene bisimide dyes. Appl Phys A 2009, 95, 285. <http://dx.doi.org/10.1007/s00339-008-5013-1>
  • Chan Julian M. W., Tischler Jonathan R., Kooi Steve E., Bulović Vladimir, Swager Timothy M.: Synthesis of J-Aggregating Dibenz[a,j]anthracene-Based Macrocycles. J Am Chem Soc 2009, 131, 5659. <http://dx.doi.org/10.1021/ja900382r>
  • Kaiser Theo E., Stepanenko Vladimir, Würthner Frank: Fluorescent J-Aggregates of Core-Substituted Perylene Bisimides: Studies on Structure−Property Relationship, Nucleation−Elongation Mechanism, and Sergeants-and-Soldiers Principle. J Am Chem Soc 2009, 131, 6719. <http://dx.doi.org/10.1021/ja900684h>
  • Chen Zhijian, Lohr Andreas, Saha-Möller Chantu R., Würthner Frank: Self-assembled π-stacks of functional dyes in solution: structural and thermodynamic features. Chem Soc Rev 2009, 38, 564. <http://dx.doi.org/10.1039/b809359h>
  • Tuccitto N., Delfanti I., Torrisi V., Scandola F., Chiorboli C., Stepanenko V., Würthner F., Licciardello A.: Supramolecular self-assembled multilayers of terpyridine-functionalized perylene bisimide metal complexes. Phys Chem Chem Phys 2009, 11, 4033. <http://dx.doi.org/10.1039/b819711n>
  • Mikroyannidis John A., Stylianakis Minas M., Suresh P., Roy M. S., Sharma G. D.: Synthesis of perylene monoimide derivative and its use for quasi-solid-state dye-sensitized solar cells based on bare and modified nano-crystalline ZnO photoelectrodes. Energy Environ Sci 2009, 2, 1293. <http://dx.doi.org/10.1039/b915235k>
  • Kowerko Danny, Schuster Jörg, von Borczyskowski Christian: Restricted conformation dynamics of single functionalized perylene bisimide molecules on SiO2 surfaces and in thin polymer films. Molec Phys 2009, 107, 1911. <http://dx.doi.org/10.1080/00268970902758631>
  • Würthner Frank, Bauer Christoph, Stepanenko Vladimir, Yagai Shiki: A Black Perylene Bisimide Super Gelator with an Unexpected J-Type Absorption Band. Adv Mater 2008, 20, 1695. <http://dx.doi.org/10.1002/adma.200702935>
  • Yagai Shiki, Seki Tomohiro, Karatsu Takashi, Kitamura Akihide, Würthner Frank: Transformation from H- to J-Aggregated Perylene Bisimide Dyes by Complexation with Cyanurates. Angew Chem 2008, 120, 3415. <http://dx.doi.org/10.1002/ange.200705385>
  • Yagai Shiki, Seki Tomohiro, Karatsu Takashi, Kitamura Akihide, Würthner Frank: Transformation from H- to J-Aggregated Perylene Bisimide Dyes by Complexation with Cyanurates. Angew Chem Int Ed 2008, 47, 3367. <http://dx.doi.org/10.1002/anie.200705385>
  • Ghosh Suhrit, Li Xue-Qing, Stepanenko Vladimir, Würthner Frank: Control of H- and J-Type π Stacking by Peripheral Alkyl Chains and Self-Sorting Phenomena in Perylene Bisimide Homo- and Heteroaggregates. Chem Eur J 2008, 14, 11343. <http://dx.doi.org/10.1002/chem.200801454>
  • Cooke Michael W., Chartrand Daniel, Hanan Garry S.: Self-assembly of discrete metallosupramolecular luminophores. Coord Chem Rev - 2008, 252, 903. <http://dx.doi.org/10.1016/j.ccr.2008.01.006>
  • Fron Eduard, Pilot Roberto, Schweitzer Gerd, Qu Jianqiang, Herrmann Andreas, Müllen Klaus, Hofkens Johan, Van der Auweraer Mark, De Schryver Frans C.: Photoinduced electron-transfer in perylenediimide triphenylamine-based dendrimers: single photon timing and femtosecond transient absorption spectroscopy. Photochem Photobiol Sci 2008, 7, 597. <http://dx.doi.org/10.1039/b718479d>
  • Fron Eduard, Schweitzer Gerd, Osswald Peter, Würthner Frank, Marsal Philippe, Beljonne David, Müllen Klaus, De Schryver Frans C., Van der Auweraer Mark: Photophysical study of bay substituted perylenediimides. Photochem Photobiol Sci 2008, 7, 1509. <http://dx.doi.org/10.1039/b813737d>
  • Kaiser Theo E., Wang Hao, Stepanenko Vladimir, Würthner Frank: Supramolecular Construction of Fluorescent J-Aggregates Based on Hydrogen-Bonded Perylene Dyes. Angew Chem 2007, 119, 5637. <http://dx.doi.org/10.1002/ange.200701139>
  • Kaiser Theo E., Wang Hao, Stepanenko Vladimir, Würthner Frank: Supramolecular Construction of Fluorescent J-Aggregates Based on Hydrogen-Bonded Perylene Dyes. Angew Chem Int Ed 2007, 46, 5541. <http://dx.doi.org/10.1002/anie.200701139>
  • Osswald Peter, Würthner Frank: Conformational Effects of Bay Substituents on Optical, Electrochemical and Dynamic Properties of Perylene Bisimides: Macrocyclic Derivatives as Effective Probes. Chem Eur J 2007, 13, 7395. <http://dx.doi.org/10.1002/chem.200700601>
  • Lang Erwin, Hildner Richard, Engelke Hanna, Osswald Peter, Würthner Frank, Köhler Jürgen: Comparison of the Photophysical Parameters for Three Perylene Bisimide Derivatives by Single-Molecule Spectroscopy. Chem Eur J of Chem Phys 2007, 8, 1487. <http://dx.doi.org/10.1002/cphc.200700186>
  • Su Wei, Zhang Yuexing, Zhao Chuntao, Li Xiyou, Jiang Jianzhuang: Self-Assembled Organic Nanostructures: Effect of Substituents on the Morphology. Chem Eur J of Chem Phys 2007, 8, 1857. <http://dx.doi.org/10.1002/cphc.200700246>