Energy and Electron Transfer Dynamics within a Series of Perylene Diimide/Cyclophane Systems

Ryan, Seán T.  J.; Young, Ryan M.; Henkelis, James J.; Hafezi, Nema; Vermeulen, Nicolaas A.; Hennig, Andreas; Dale, Edward J.; Wu, Yilei; Krzyaniak, Matthew D.; Fox, Athan; Nau, Werner M.; Wasielewski, Michael R.; Stoddart, J. Fraser; Scherman, Oren A.

doi:10.1021/jacs.5b10329

Title: Energy and Electron Transfer Dynamics within a Series of Perylene Diimide/Cyclophane Systems

Journal Article · Mon Nov 09 00:00:00 EST 2015 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.5b10329· OSTI ID:1387520

Ryan, Seán T. J. ^[1]; Young, Ryan M. ^[2]; Henkelis, James J. ^[3]; Hafezi, Nema ^[3]; Vermeulen, Nicolaas A. ^[3]; Hennig, Andreas ^[4]; Dale, Edward J. ^[3]; Wu, Yilei ^[2]; Krzyaniak, Matthew D. ^[2]; Fox, Athan ^[1]; Nau, Werner M. ^[4]; Wasielewski, Michael R. ^[2]; Stoddart, J. Fraser ^[3]; Scherman, Oren A. ^[1]

Univ. of Cambridge (United Kingdom)
Northwestern Univ., Evanston, IL (United States); Energy Frontier Research Centers (EFRC) (United States). Argonne-Northwestern Solar Energy Research Center (ANSER)
Northwestern Univ., Evanston, IL (United States)
Jacobs Univ. Bremen (Germany)

Artificial photosynthetic systems for solar energy conversion exploit both covalent and supramolecular chemistry to produce favorable arrangements of light-harvesting and redox-active chromophores in space. An understanding of the interplay between key processes for photosynthesis, namely light-harvesting, energy transfer, and photoinduced charge separation and the design of novel, self-assembling components capable of these processes are imperative for the realization of multifunctional integrated systems. Herein we report our investigations on the potential of extended tetracationic cyclophane/perylene diimide systems as components for artificial photosynthetic applications. We show how the selection of appropriate heterocycles, as extending units, allows for tuning of the electron accumulation and photophysical properties of the extended tetracationic cyclophanes. Spectroscopic techniques confirm energy transfer between the extended tetracationic cyclophanes and perylene diimide is ultrafast and quantitative, while the heterocycle specifically influences the energy transfer related parameters and the acceptor excited state.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Argonne-Northwestern Solar Energy Research Center (ANSER)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); Cambridge Home and European Scholarship Scheme; Robert Gardiner Memorial Scholarship; European Research Council (ERC); Engineering and Physical Sciences Research Council (EPSRC); Joint Center of Excellence in Integrated Nano-Systems (JCIN); National Science Foundation (NSF); German Research Foundation (DFG)

Grant/Contract Number:: SC0001059; NA-686/5

OSTI ID:: 1387520

Journal Information:: Journal of the American Chemical Society, Vol. 137, Issue 48; Related Information: ANSER partners with Northwestern University (lead); Argonne National Laboratory; University of Chicago; University of Illinois, Urbana-Champaign; Yale University; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 58 works

Citation information provided by
Web of Science

References (43)

Ruthenium Photocatalysts Capable of Reversibly Storing up to Four Electrons in a Single Acceptor Ligand: A Step Closer to Artificial Photosynthesis Konduri, Rama; Ye, Hongwei; MacDonnell, Frederick M. Angewandte Chemie International Edition, Vol. 41, Issue 17 https://doi.org/10.1002/1521-3773(20020902)41:17<3185::AID-ANIE3185>3.0.CO;2-Z	journal	September 2002
Synthesis and characterization of new conjugation-extended viologens involving a central aromatic linking group Takahashi, Kazuko; Nihira, Takayasu; Akiyama, Kimio Journal of the Chemical Society, Chemical Communications, Issue 8 https://doi.org/10.1039/c39920000620	journal	January 1992
The Glaser reaction mechanism. A DFT study Fomina, Lioudmila; Vazquez, Blanca; Tkatchouk, Ekaterina Tetrahedron, Vol. 58, Issue 33 https://doi.org/10.1016/S0040-4020(02)00669-5	journal	August 2002
Three-dimensional structure of plant light-harvesting complex determined by electron crystallography K¨hlbrandt, Werner; Wang, Da Neng Nature, Vol. 350, Issue 6314 https://doi.org/10.1038/350130a0	journal	March 1991
High hopes: can molecular electronics realise its potential? Coskun, Ali; Spruell, Jason M.; Barin, Gokhan Chemical Society Reviews, Vol. 41, Issue 14 https://doi.org/10.1039/c2cs35053j	journal	January 2012
Efficient Host–Guest Energy Transfer in Polycationic Cyclophane–Perylene Diimide Complexes in Water Ryan, Seán T. J.; Del Barrio, Jesús; Ghosh, Indrajit Journal of the American Chemical Society, Vol. 136, Issue 25 https://doi.org/10.1021/ja5032437	journal	June 2014
Principles of Fluorescence Spectroscopy Lakowicz, Joseph R. Springer New York, NY https://doi.org/10.1007/978-0-387-46312-4	book	January 2006
Putting Mechanically Interlocked Molecules (MIMs) to Work in Tomorrow’s World Stoddart, J. Fraser Angewandte Chemie International Edition, Vol. 53, Issue 42 https://doi.org/10.1002/anie.201408043	journal	September 2014
Stabilizing triplet excited states for ultralong organic phosphorescence An, Zhongfu; Zheng, Chao; Tao, Ye Nature Materials, Vol. 14, Issue 7 https://doi.org/10.1038/nmat4259	journal	April 2015
Photochemistry of 3,4,9,10-perylenetetracarboxylic dianhydride dyes. 3. Singlet and triplet excited-state properties of the bis(2,5-di-tert-butylphenyl)imide derivative Ford, William E.; Kamat, Prashant V. The Journal of Physical Chemistry, Vol. 91, Issue 25 https://doi.org/10.1021/j100309a012	journal	December 1987
A Theory of Sensitized Luminescence in Solids Dexter, D. L. The Journal of Chemical Physics, Vol. 21, Issue 5, p. 836-850 https://doi.org/10.1063/1.1699044	journal	May 1953
Triplet photosensitizers: from molecular design to applications Zhao, Jianzhang; Wu, Wanhua; Sun, Jifu Chemical Society Reviews, Vol. 42, Issue 12 https://doi.org/10.1039/c3cs35531d	journal	January 2013
Supramolecular Electrochemistry Kaifer, Angel; Gómez‐Kaifer, Marielle https://doi.org/10.1002/9783527613601	journal	September 1999
Molecular Catenanes, Rotaxanes and Knots Sauvage, J. ‐P.; Dietrich‐Buchecker, C. https://doi.org/10.1002/9783527613724	book	June 1999
Octopolar Chromophores Based on Donor- and Acceptor-Substituted 1,3,5-Tris(phenylethynyl)benzenes: Impact of meta -Conjugation on the Molecular and Electronic Structure by Means of Spectroscopy and Theory Oliva, María Moreno; Casado, Juan; Hennrich, Gunther The Journal of Physical Chemistry B, Vol. 110, Issue 39 https://doi.org/10.1021/jp0627269	journal	October 2006
Atomic model of plant light-harvesting complex by electron crystallography Kühlbrandt, Werner; Wang, Da Neng; Fujiyoshi, Yoshinori Nature, Vol. 367, Issue 6464 https://doi.org/10.1038/367614a0	journal	February 1994
Zwischenmolekulare Energiewanderung und Fluoreszenz Förster, Th. Annalen der Physik, Vol. 437, Issue 1-2, p. 55-75 https://doi.org/10.1002/andp.19484370105	journal	January 1948
Perylene-3,4,9,10-tetracarboxylic Acid Diimides: Synthesis, Physical Properties, and Use in Organic Electronics Huang, Chun; Barlow, Stephen; Marder, Seth R. The Journal of Organic Chemistry, Vol. 76, Issue 8 https://doi.org/10.1021/jo2001963	journal	April 2011
Photosynthetic Light-Harvesting Pigment−Protein Complexes: Toward Understanding How and Why Pullerits, Tõnu; Sundström, Villy Accounts of Chemical Research, Vol. 29, Issue 8 https://doi.org/10.1021/ar950110o	journal	January 1996
ExBox: A Polycyclic Aromatic Hydrocarbon Scavenger Barnes, Jonathan C.; Juríček, Michal; Strutt, Nathan L. Journal of the American Chemical Society, Vol. 135, Issue 1 https://doi.org/10.1021/ja307360n	journal	October 2012
Syntheses and Dynamics of Donor−Acceptor [2]Catenanes in Water Fang, Lei; Basu, Subhadeep; Sue, Chi-Hau Journal of the American Chemical Society, Vol. 133, Issue 3 https://doi.org/10.1021/ja1087562	journal	January 2011
Many wheels make light work Kühlbrandt, Werner Nature, Vol. 374, Issue 6522 https://doi.org/10.1038/374497a0	journal	April 1995
Crystal structure of an integral membrane light-harvesting complex from photosynthetic bacteria McDermott, G.; Prince, S. M.; Freer, A. A. Nature, Vol. 374, Issue 6522 https://doi.org/10.1038/374517a0	journal	April 1995
Rylene and Related Diimides for Organic Electronics Zhan, Xiaowei; Facchetti, Antonio; Barlow, Stephen Advanced Materials, Vol. 23, Issue 2, p. 268-284 https://doi.org/10.1002/adma.201001402	journal	December 2010
Self-assembling hydrogel scaffolds for photocatalytic hydrogen production Weingarten, Adam S.; Kazantsev, Roman V.; Palmer, Liam C. Nature Chemistry, Vol. 6, Issue 11 https://doi.org/10.1038/nchem.2075	journal	October 2014
Effect of spin orbit interactions on the dipolar nature of the radiative microwave zero‐field transitions in aromatic molecules El‐Sayed, M. A. The Journal of Chemical Physics, Vol. 60, Issue 11 https://doi.org/10.1063/1.1680930	journal	June 1974
Reduction of aryl halides by consecutive visible light-induced electron transfer processes Ghosh, I.; Ghosh, T.; Bardagi, J. I. Science, Vol. 346, Issue 6210 https://doi.org/10.1126/science.1258232	journal	November 2014
Photochemical heavy-atom effects Koziar, Joseph C.; Cowan, Dwaine O. Accounts of Chemical Research, Vol. 11, Issue 9 https://doi.org/10.1021/ar50129a003	journal	September 1978
Dynamic hook-and-eye nanoparticle sponges Klajn, Rafal; Olson, Mark A.; Wesson, Paul J. Nature Chemistry, Vol. 1, Issue 9 https://doi.org/10.1038/nchem.432	journal	November 2009
Polyphenylene-Based Materials for Organic Photovoltaics Li, Chen; Liu, Miaoyin; Pschirer, Neil G. Chemical Reviews, Vol. 110, Issue 11 https://doi.org/10.1021/cr100052z	journal	November 2010
Design Considerations for a System for Photocatalytic Hydrogen Production from Water Employing Mixed-Metal Photochemical Molecular Devices for Photoinitiated Electron Collection Arachchige, Shamindri M.; Brown, Jared R.; Chang, Eric Inorganic Chemistry, Vol. 48, Issue 5 https://doi.org/10.1021/ic8017387	journal	March 2009
Oxidative Coupling of Acetylenes. II ¹ Hay, Allan S. The Journal of Organic Chemistry, Vol. 27, Issue 9 https://doi.org/10.1021/jo01056a511	journal	September 1962
Strongly Fluorescent, Switchable Perylene Bis(diimide) Host-Guest Complexes with Cucurbit[8]uril In Water Biedermann, Frank; Elmalem, Einat; Ghosh, Indrajit Angewandte Chemie International Edition, Vol. 51, Issue 31 https://doi.org/10.1002/anie.201202385	journal	June 2012
Monopole effects on electronic excitation interactions between large molecules. I. Application to energy transfer in chlorophylls Chang, Jane C. The Journal of Chemical Physics, Vol. 67, Issue 9 https://doi.org/10.1063/1.435427	journal	January 1999
Excited State, Charge Transfer, and Spin Dynamics in DNA Hairpin Conjugates with Perylenediimide Hairpin Linkers Carmieli, Raanan; Zeidan, Tarek A.; Kelley, Richard F. The Journal of Physical Chemistry A, Vol. 113, Issue 16 https://doi.org/10.1021/jp900230q	journal	February 2009
Carbon-Free Energy - Vision or Utopia? Quaschning, Volker Renewable Energy and Climate Change https://doi.org/10.1002/9781119994381.ch4	book	February 2010
Highly efficient phosphorescent emission from organic electroluminescent devices Baldo, M. A.; O'Brien, D. F.; You, Y. Nature, Vol. 395, Issue 6698, p. 151-154 https://doi.org/10.1038/25954	journal	September 1998
Electron Transfer and Multi-Electron Accumulation in ExBox ⁴⁺ Dyar, Scott M.; Barnes, Jonathan C.; Juríček, Michal Angewandte Chemie International Edition, Vol. 53, Issue 21 https://doi.org/10.1002/anie.201402444	journal	May 2014
Ultrafast Conformational Dynamics of Electron Transfer in ExBox ⁴⁺ ⊂Perylene Young, Ryan M.; Dyar, Scott M.; Barnes, Jonathan C. The Journal of Physical Chemistry A, Vol. 117, Issue 47 https://doi.org/10.1021/jp409883a	journal	November 2013
Modification of Nanocrystalline WO ₃ with a Dicationic Perylene Bisimide: Applications to Molecular Level Solar Water Splitting Ronconi, Federico; Syrgiannis, Zois; Bonasera, Aurelio Journal of the American Chemical Society, Vol. 137, Issue 14 https://doi.org/10.1021/jacs.5b01519	journal	April 2015
Photoalkylation of 10-Alkylacridinium Ion via a Charge-Shift Type of Photoinduced Electron Transfer Controlled by Solvent Polarity Fukuzumi, Shunichi; Ohkubo, Kei; Suenobu, Tomoyoshi Journal of the American Chemical Society, Vol. 123, Issue 35 https://doi.org/10.1021/ja004311l	journal	September 2001
Triplet State Formation in Photoexcited Slip-Stacked Perylene-3,4:9,10-bis(dicarboximide) Dimers on a Xanthene Scaffold Lefler, Kelly M.; Brown, Kristen E.; Salamant, Walter A. The Journal of Physical Chemistry A, Vol. 117, Issue 40 https://doi.org/10.1021/jp4083008	journal	September 2013
Cyclization and Catenation Directed by Molecular Self-Assembly Wang, Wei; Wang, LiQiong; Palmer, Bruce J. Journal of the American Chemical Society, Vol. 128, Issue 34 https://doi.org/10.1021/ja061826p	journal	August 2006

Cited By (9)

Coexistence of distinct intramolecular electron transfer pathways in polyoxometalate based molecular triads Luo, Yusen; Wächtler, Maria; Barthelmes, Kevin Physical Chemistry Chemical Physics, Vol. 20, Issue 17 https://doi.org/10.1039/c8cp01007b	journal	January 2018
Perylene Diimide Based Imine Cages for Inclusion of Aromatic Guest Molecules and Visible‐Light Photocatalysis Feng, Xiying; Liao, Peisen; Jiang, Jingxing ChemPhotoChem, Vol. 3, Issue 10 https://doi.org/10.1002/cptc.201900058	journal	July 2019
From anthraquinone to heterocoronene as stable red chromophore Duan, Ruomeng; Schollmeyer, Dieter; Müllen, Klaus Journal of Materials Chemistry C, Vol. 6, Issue 6 https://doi.org/10.1039/c7tc05073a	journal	January 2018
Influence of imide-substituents on the H-type aggregates of perylene diimides bearing cetyloxy side-chains at bay positions Raj, Michael Ruby; Margabandu, Rajamani; Mangalaraja, Ramalinga Viswanathan Soft Matter, Vol. 13, Issue 48 https://doi.org/10.1039/c7sm01918a	journal	January 2017
Halogen bonding influences perylene-core twists in non-core substituted perylene tetraesters Wojciechowski, Jonathan P.; Martin, Adam D.; Bhadbhade, Mohan CrystEngComm, Vol. 18, Issue 24 https://doi.org/10.1039/c6ce00929h	journal	January 2016
Structure and luminescence properties of supramolecular polymers of amphiphilic aromatic thioether–peptide conjugates in water Ahlers, Patrick; Götz, Christian; Riebe, Steffen Polymer Chemistry, Vol. 10, Issue 23 https://doi.org/10.1039/c8py01712c	journal	January 2019
Two-Component Fluorescent-Semiconducting Hydrogel from Naphthalene Diimide-Appended Peptide with Long-Chain Amines: Variation in Thermal and Mechanical Strengths of Gels Nandi, Nibedita; Basak, Shibaji; Kirkham, Steven Langmuir, Vol. 32, Issue 49 https://doi.org/10.1021/acs.langmuir.6b02727	journal	November 2016
Novel dithiano-thieno fused perylene diimides: synthesis, characterization and application in organic thin-film transistors (OTFTs) Li, Gang; Li, Dandan; Liu, Xitong Chemical Communications, Vol. 55, Issue 65 https://doi.org/10.1039/c9cc04133h	journal	January 2019
Broad-Spectrum Tunable Photoluminescent Nanomaterials Constructed from a Modular Light-Harvesting Platform Based on Macrocyclic Amphiphiles Xu, Zhe; Peng, Shu; Wang, Yu-Ying Advanced Materials, Vol. 28, Issue 35 https://doi.org/10.1002/adma.201601719	journal	June 2016

Linked Research (4)

Figures / Tables (12)

Similar Records

Intramolecular Energy and Electron Transfer within a Diazaperopyrenium-Based Cyclophane

Journal Article · Fri Mar 10 00:00:00 EST 2017 · Journal of the American Chemical Society · OSTI ID:1387520

Gong, Xirui; Young, Ryan M.; Hartlieb, Karel J.; +13 more

Synthesis of arrays containing porphyrin, chlorin, and perylene-imide constituents for panchromatic light-harvesting and charge separation

Journal Article · Mon Jan 01 00:00:00 EST 2018 · RSC Advances · OSTI ID:1387520

Hu, Gongfang; Kang, Hyun Suk; Mandal, Amit Kumar; +5 more

Long-Lived Charge Separation at Heterojunctions between Semiconducting Single-Walled Carbon Nanotubes and Perylene Diimide Electron Acceptors

Journal Article · Fri Apr 13 00:00:00 EDT 2018 · Journal of Physical Chemistry. C · OSTI ID:1387520

Kang, Hyun Suk; Sisto, Thomas J.; Peurifoy, Samuel; +4 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
catalysis (homogeneous)
catalysis (heterogeneous)
solar (photovoltaic)
solar (fuels)
photosynthesis (natural and artificial)
bio-inspired
hydrogen and fuel cells
electrodes - solar
defects
charge transport
spin dynamics
membrane
materials and chemistry by design
optics
synthesis (novel materials)
synthesis (self-assembly)
redox reactions
quantum mechanics
absorption
fluorescence
excited states

CCDC 1054607: Experimental Crystal Structure Determination Ryan, Seán T. J.; Young, Ryan M.; Henkelis, James J. https://doi.org/10.5517/cc14ddlj The current record is supplemented by this dataset	dataset	January 2016
CCDC 1402176: Experimental Crystal Structure Determination Ryan, Seán T. J.; Young, Ryan M.; Henkelis, James J. https://doi.org/10.5517/cc1j22h5 The current record is supplemented by this dataset	dataset	January 2016
CCDC 1402175: Experimental Crystal Structure Determination Ryan, Seán T. J.; Young, Ryan M.; Henkelis, James J. https://doi.org/10.5517/cc1j22g4 The current record is supplemented by this dataset	dataset	January 2016
CCDC 1054606: Experimental Crystal Structure Determination Ryan, Seán T. J.; Young, Ryan M.; Henkelis, James J. https://doi.org/10.5517/cc14ddkh The current record is supplemented by this dataset	dataset	January 2016