Synthesis, Ensemble, and Single Molecule Characterization of a Diphenyl-Acetylene Linked Terrylenediimide Dimer.

The synthesis and the photophysical characterization at the ensemble and single molecule level of a terrylenediimide (TDI) dimer are reported. The spectroscopic experimental data are compared with those obtained for the corresponding model compound TDI. Steady-state and ps time-correlated single photon counting have shown that both chromophores in the TDI dimer are in the weak coupling regime allowing their interaction by Förster resonance energy transfer. Femtosecond transient absorption experiments showed an excitation power dependence of the fluorescence decay, which could indicate the occurrence of singlet-singlet annihilation. Single molecule intensity traces were investigated for the TDI dimer and suggested two intensity levels. For both intensity levels several parameters among which emission maximum, fluorescence decay times, antibunching, blinking off-times and rate of dark state formation were compared. The blinking analysis revealed that the yield of dark state formation is an order of magnitude higher when the two chromophores are still active compared to the case where one is photobleached. The off-times remain however similar.

[1]  M. Kuo,et al.  Solution-processed single-crystal perylene diimide transistors with high electron mobility , 2015 .

[2]  J. Waluk,et al.  In Search for the Best Environment for Single Molecule Studies: Photostability of Single Terrylenediimide Molecules in Various Polymer Matrices. , 2015, The journal of physical chemistry letters.

[3]  L. Wang,et al.  An alcohol-soluble perylene diimide derivative as cathode interfacial layer for PDI-based nonfullerene organic solar cells , 2015 .

[4]  Qichun Zhang,et al.  Synthesis, Characterization, Physical Properties, and OLED Application of Single BN-Fused Perylene Diimide. , 2015, The Journal of organic chemistry.

[5]  J. Hofkens,et al.  Photophysical investigation of cyano-substituted terrylenediimide derivatives. , 2014, The journal of physical chemistry. B.

[6]  J. Hofkens,et al.  A surface-bound molecule that undergoes optically biased Brownian rotation. , 2014, Nature nanotechnology.

[7]  K. Müllen,et al.  Green emitting photoproducts from terrylene diimide after red illumination. , 2013, Journal of the American Chemical Society.

[8]  J. Hofkens,et al.  Energy transfer pathways in a rylene-based Triad. , 2011, Chemphyschem : a European journal of chemical physics and physical chemistry.

[9]  K. Müllen,et al.  Photoblinking and photobleaching of rylene diimide dyes. , 2011, Physical chemistry chemical physics : PCCP.

[10]  T. Weil,et al.  The rylene colorant family--tailored nanoemitters for photonics research and applications. , 2010, Angewandte Chemie.

[11]  Alois Renn,et al.  Single-Molecule Sensitivity in Optical Absorption at Room Temperature , 2010 .

[12]  H. Hioki,et al.  Coexpression of VGLUT1 and VGLUT2 in trigeminothalamic projection neurons in the principal sensory trigeminal nucleus of the rat , 2010, The Journal of comparative neurology.

[13]  Peter Dedecker,et al.  Spectroscopic rationale for efficient stimulated-emission depletion microscopy fluorophores. , 2010, Journal of the American Chemical Society.

[14]  M. Wasielewski,et al.  Photophysics and redox properties of rylene imide and diimide dyes alkylated ortho to the imide groups. , 2010, The journal of physical chemistry. B.

[15]  K. Müllen,et al.  Single molecule probing of the local segmental relaxation dynamics in polymer above the glass transition temperature. , 2009, Journal of the American Chemical Society.

[16]  Dong Ha Kim,et al.  Synthesis, ensemble, and single molecule characterization of a diphenyl-acetylene linked perylenediimide trimer , 2009 .

[17]  John T. M. Kennis,et al.  Ultrafast transient absorption spectroscopy: principles and application to photosynthetic systems , 2009, Photosynthesis Research.

[18]  E. Fron,et al.  Photophysical study of bay substituted perylenediimides , 2008 .

[19]  K. Müllen,et al.  Intramolecular electronic excitation energy transfer in donor/acceptor dyads studied by time and frequency resolved single molecule spectroscopy. , 2008, The Journal of chemical physics.

[20]  David Beljonne,et al.  Does Förster theory predict the rate of electronic energy transfer for a model dyad at low temperature? , 2008, The journal of physical chemistry. B.

[21]  Jens Michaelis,et al.  Diffusion of oriented single molecules with switchable mobility in networks of long unidimensional nanochannels. , 2008, Journal of the American Chemical Society.

[22]  T. Bein,et al.  Visualizing single-molecule diffusion in mesoporous materials , 2007, Nature.

[23]  J. Hofkens,et al.  Single perylene diimide dendrimers as single-photon sources , 2007 .

[24]  S. Hell.  Far-Field Optical Nanoscopy , 2007, Science.

[25]  J. Hofkens,et al.  Energy and Electron Transfer in Ethynylene Bridged Perylene Diimide Multichromophores , 2007 .

[26]  Jiyoul Lee,et al.  Studies on poly(methyl methacrylate) dielectric layer for field effect transistor: Influence of polymer tacticity , 2007 .

[27]  J. Hofkens,et al.  CT-CT annihilation in rigid perylene end-capped pentaphenylenes. , 2007, Journal of the American Chemical Society.

[28]  J. Hofkens,et al.  Origin of simultaneous donor-acceptor emission in single molecules of peryleneimide-terrylenediimide labeled polyphenylene dendrimers. , 2007, The journal of physical chemistry. B.

[29]  T. Tachikawa,et al.  Single-molecule detection of airborne singlet oxygen. , 2006, Journal of the American Chemical Society.

[30]  J. Hofkens,et al.  Charge transfer enhanced annihilation leading to deterministic single photon emission in rigid perylene end-capped polyphenylenes. , 2005, Chemical communications.

[31]  J. Hofkens,et al.  Energy dissipation in multichromophoric single dendrimers. , 2005, Accounts of chemical research.

[32]  J. Hofkens,et al.  Higher-excited-state photophysical pathways in multichromophoric systems revealed by single-molecule fluorescence spectroscopy. , 2004, Chemphyschem : a European journal of chemical physics and physical chemistry.

[33]  Michael W. Holman,et al.  Studying and switching electron transfer: from the ensemble to the single molecule. , 2004, Journal of the American Chemical Society.

[34]  J. Hofkens,et al.  Multichromophoric dendrimers as single-photon sources: A single-molecule study , 2004 .

[35]  Boris Rybtchinski,et al.  Ultrafast aggregate-to-aggregate energy transfer within self-assembled light-harvesting columns of zinc phthalocyanine tetrakis(perylenediimide). , 2004, Journal of the American Chemical Society.

[36]  Stefan Sax,et al.  Ladder-type pentaphenylenes and their polymers: efficient blue-light emitters and electron-accepting materials via a common intermediate. , 2004, Journal of the American Chemical Society.

[37]  Kenneth D. Weston,et al.  Revealing competitive Förster-type resonance energy-transfer pathways in single bichromophoric molecules , 2003, Proceedings of the National Academy of Sciences of the United States of America.

[38]  T. Weil,et al.  Energy transfer within perylene-terrylene dendrimers evidenced by polychromatic transient absorption measurements , 2003, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[39]  Mircea Cotlet,et al.  Antibunching in the emission of a single tetrachromophoric dendritic system. , 2002, Journal of the American Chemical Society.

[40]  T. Weil,et al.  Conformational rearrangements in and twisting of a single molecule , 2001 .

[41]  Mark Van der Auweraer,et al.  New picosecond laser system for easy tunability over the whole ultraviolet/visible/near infrared wavelength range based on flexible harmonic generation and optical parametric oscillation , 2001 .

[42]  W. Göhde,et al.  Influence of oxygen on single molecule blinking , 1998 .

[43]  P. Barbara,et al.  Classifying the Photophysical Dynamics of Single- and Multiple-Chromophoric Molecules by Single Molecule Spectroscopy , 1998 .

[44]  M. A. Bopp,et al.  Fluorescence and photobleaching dynamics of single light-harvesting complexes. , 1997, Proceedings of the National Academy of Sciences of the United States of America.

[45]  Paul F. Barbara,et al.  Discrete Intensity Jumps and Intramolecular Electronic Energy Transfer in the Spectroscopy of Single Conjugated Polymer Molecules , 1997 .

[46]  R. Marcus.  On the Theory of Shifts and Broadening of Electronic Spectra of Polar Solutes in Polar Media , 1965 .

[47]  N. Mataga,et al.  Solvent Effects upon Fluorescence Spectra and the Dipolemoments of Excited Molecules , 1956 .

[48]  N. Mataga,et al.  The Solvent Effect on Fluorescence Spectrum, Change of Solute-Solvent Interaction during the Lifetime of Excited Solute Molecule , 1955 .

[49]  Ernst Lippert,et al.  Dipolmoment und Elektronenstruktur von angeregten Molekülen , 1955 .

[50]  Yang Chuan-lu,et al.  Electron Transport Properties of DiphenylacetyleneMolecular Wire , 2008 .

[51]  Mark Van der Auweraer,et al.  One-dimensional J-aggregates: Dependence of the properties of the exciton band on the model of the intermolecular coupling , 2002 .