Abstract
Two novel quinacridone (QA) cyclophanes with intrinsic intramolecular dye-dye interactions have been designed and synthesized. X-ray crystal structures as well as detailed photophysical properties have been well demonstrated. These two dyes have a major advantage that efficient fluorescence quenching can be observed even in their dilute solutions. A comparison of photophysical properties between the dimeric QA cyclophane and its reference monomeric counterpart indicates that the dimerization is predominant for the fluorescence quenching of QA dyes in solution. This study provided some model QA derivatives with dimeric structures for understanding the fluorescence quenching of QA dyes in solutions.
Similar content being viewed by others
References
Hiramoto M, Kawase S, Yokoyama M. Photoinduced hole injection multiplication in p-type quinacridone pigment films. Jpn J Appl Phys, 1996, 35: L349–L351
Shichiri T, Suezaki M, Inoue T. Three-layer organic solar cell. Chem Lett, 1992, 1717–1720
Nakahara H, Kitahara K, Nishi H, Fukuda K. Orientation control of quinacridone derivatives with long alkyl chains in Langmuir-Blodgett films. Chem Lett, 1992, 711–714
Nakahara H, Fukuda K, Ikeda M, Kitahara K, Nishi H. Langmuir-Blodgett films of polyheterocyclic compounds with long alkyl chains. Thin Solid Films, 1992, 210/211: 555–558
Chen JJ-A, Chen TL, Kim B, Poulsen DA, Mynar JL, Fréchet JMJ, Ma B. Quinacridone-based molecular donors for solution processed bulk-heterojunction organic solar cells. Appl Mater Interf, 2010, 2: 2679–2686
Pho TV, Zalar P, Garcia A, Nguyen TQ, Wudl F. Electron injection barrier reduction for organic light-emitting devices by quinacridone derivatives. Chem Commun, 2010, 46: 8210–8212
Keller U, Müllen K, De Feyter S, De Schryver FC. Hydrogen-bonding and phase-forming behavior of a soluble quinacridone. Adv Mater, 1996, 8: 490–496
Feyter SD, Gesquière A, De Schryver FC, Keller U, Müllen K. Aggregation properties of soluble quinacridones in two and three dimensions. Chem Mater, 2002, 14: 989–997
Shaheen SE, Kippelen B, Peyghambarian N, Wang JF, Anderson JD, Mash EA, Lee PA, Armstrong NR, Kawabe YJ. Energy and charge transfer in organic light-emitting diodes: A soluble quinacridone study. Appl Phys, 1999, 85: 7939–7945
Flora WH, Hall HK, Armatrong NR. Guest emission processes in doped organic light-emitting diodes: Use of phthalocyanine and naphthalocyanine near-IR dopants. J Phys Chem B, 2003, 107: 1142–1150
Freeman AW, Koene SC, Malenfant PRL, Thompson ME, Frechet JMJ. Dendrimer-containing light-emitting diodes: Toward site-isolation of chromophores. J Am Chem Soc, 2000, 122: 12385–12386
Shi J, Tang CW. Doped organic electroluminescent devices with im proved stability. Appl Phys Lett, 1997, 70: 1665–1667
Bi H, Ye KQ, Zhao YF, Yang Y, Liu Y, Wang Y. Fluorinated quinacridone derivitives based organic light-emitting device with high power efficiency. Org Electron, 2010, 11: 1180–1184
Aziz H, Popovic ZD, Hu NX. Organic light emitting devices with enhanced operational stability at elevated temperatures. Appl Phys Lett, 2002, 81: 370–372
Gross EM, Anderson JD, Slaterbeck AF, Thayumanavan S, Barlow S, Zhang Y, Marder SR, Hall HK, Nabor MF, Wang JF, Mask EA, Armstrong NR, Wightman RM. Electrogenerated chemiluminescence from derivatives of aluminum quinolate and quinacridones: Crossreactions with triarylamines lead to singlet emission through triplettriplet annihilation pathways. J Am Chem Soc, 2000, 122: 4972–4979
Ortiz A, Flora WH, D’Ambruoso GD, Armstrong NR, McGrath DV. Dendritic incorporation of quinacridone: Solubility, electrochemistry, and solid state luminescence. Chem Commun, 2005, 444–446
Qiu D, Ye K, Wang Y, Zhou B, Zhang X, Lei SB, Wan LJ. In situ scanning tunneling microscopic investigation of the two-dimensional ordering of different alkyl chain-substituted quinacridone derivatives at highly oriented pyrolytic graphite/solution interface. Langmuir, 2003, 19: 678–681
Mu Z, Wang Z, Zhang X, Ye K, Wang Y. Influence of substituents on two-dimensional ordering of oligo(phenylene-ethynylene)s — A scanning tunneling microscopy study. Langmuir, 2004, 20: 8892–8896
Lin FD, Zhong Y, Chi LF, Ye K, Wang Y, Fuchs H. Temperaturetuned organic monolayer growth: N,N-di(n-butyl)quinacridone on Ag(110). Phys Rev B, 2006, 73: 235420
Zhao Y, Fan Y, Mu X, Gao H, Wang J, Zhang J, Yang W, Chi L, Wang Y. Self-assembly of luminescent twisted fibers based on achiral quinacridone derivatives. Nano Res, 2009, 2: 493–499
Ye K, Wang J, Sun H, Liu Y, Mu Z, Li F, Jiang S, Zhang J, Zhang H, Wang Y, Che C. Supramolecular structures and assembly and luminescent properties of quinacridone derivatives. J Phys Chem B, 2005, 109: 8008–8016
Yu D, Peng T, Zhang H, Bi H, Zhang J, Wang Y. Basket-shaped quinacridone cyclophanes: Synthesis, solid-state structures, and properties. New J Chem, 2010, 34: 2213–2219
Wang J, Zhao YF, Dou CD, Sun H, Xu P, Ye KQ, Zhang JY, Jiang SM, Li F, Wang Y. Alkyl and dendron substituted quinacridones: Synthesis, structures, and luminescent. J Phys Chem B, 2007, 111: 5082–5089
Wang J, Zhao YF, Zhang JH, Zhang JY, Yang B, Wang Y, Zhang DK, You H, Ma DG. Assembly of one-dimensional organic luminescent nanowires based on quinacridone derivatives. J Phys Chem C, 2007, 111: 9177–9183
Wang W, Han JJ, Wang LQ, Li LS, Shaw WJ, Li ADQ. Dynamic — stacked molecular assemblies emit from green to red colors. Nano Lett, 2003, 3: 455–458
Lewis FD, Wu T, Burch EL, Bassani DM, Yang JS, Schneider S, Jäger W, Letsinger RL. Hybrid oligonucleotides containing stilbene units excimer fluorescence and photodimerization. J Am Chem Soc, 1995, 117: 8785–8792
Liang K, Farahat MS, Perlstein J, Law KY, Whitten DG. Exciton interactions in nonconjugated squaraine dimers. Mechanisms for coupling and consequences for photophysics and photochemistry. J Am Chem Soc, 1997, 119: 830–831
Ros-Lis JV, Martínez-Máñez R, Soto J. Colorimetric signaling of large aromatic hydrocarbons via the enhancement of aggregation processes. Org Lett, 2005, 7: 2337–2339
Author information
Authors and Affiliations
Corresponding authors
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Yu, D., Peng, T., Javad, I. et al. Dimeric quinacridone cyclophanes: Synthesis, structures, and photophysical properties. Sci. China Chem. 54, 314–319 (2011). https://doi.org/10.1007/s11426-010-4194-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-010-4194-6