Heterocyclic Chromophore Amphiphiles and their Supramolecular Polymerization

Đorđević, Luka; Sai, Hiroaki; Yang, Yang; Sather, Nicholas A.; Palmer, Liam C.; Stupp, Samuel I.

doi:10.1002/anie.202214997

Heterocyclic Chromophore Amphiphiles and their Supramolecular Polymerization

Journal Article · Fri Mar 17 00:00:00 EDT 2023 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.202214997· OSTI ID:1962253

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Center for Bio-Inspired Energy Science Northwestern University Evanston IL 60208 USA, Department of Chemistry Northwestern University Evanston IL 60208 USA, Present address: Department of Chemical Sciences University of Padova 35131 Padova Italy
Center for Bio-Inspired Energy Science Northwestern University Evanston IL 60208 USA, Simpson Querrey Institute for BioNanotechnology Northwestern University Chicago IL 60611 USA
Simpson Querrey Institute for BioNanotechnology Northwestern University Chicago IL 60611 USA, Department of Materials Science and Engineering Northwestern University Evanston IL 60208 USA
Center for Bio-Inspired Energy Science Northwestern University Evanston IL 60208 USA, Department of Chemistry Northwestern University Evanston IL 60208 USA, Simpson Querrey Institute for BioNanotechnology Northwestern University Chicago IL 60611 USA
Center for Bio-Inspired Energy Science Northwestern University Evanston IL 60208 USA, Department of Chemistry Northwestern University Evanston IL 60208 USA, Simpson Querrey Institute for BioNanotechnology Northwestern University Chicago IL 60611 USA, Department of Materials Science and Engineering Northwestern University Evanston IL 60208 USA, Department of Medicine Northwestern University Chicago IL 60611 USA

Abstract

Supramolecular polymerization of π‐conjugated amphiphiles in water is an attractive approach to create functional nanostructures. Here, we report on the synthesis, optoelectronic and electrochemical properties, aqueous supramolecular polymerization, and conductivity of polycyclic aromatic dicarboximide amphiphiles. The chemical structure of the model perylene monoimide amphiphile was modified with heterocycles, essentially substituting one fused benzene ring with thiophene, pyridine or pyrrole rings. All the heterocycle‐containing monomers investigated underwent supramolecular polymerization in water. Large changes to the monomeric molecular dipole moments led to nanostructures with low electrical conductivity due to diminished interactions. Although the substitution of benzene with thiophene did not notably change the monomer dipole moment, it led to crystalline nanoribbons with 20‐fold higher electrical conductivity, due to enhanced dispersion interactions as a result of the presence of sulfur atoms.

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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS); Energy Frontier Research Centers (EFRC) (United States). Center for Bio-Inspired Energy Science (CBES); Northwestern Univ., Evanston, IL (United States)

Sponsoring Organization:: National Science Foundation (NSF); USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC02-06CH11357; SC0000989

OSTI ID:: 1962253

Alternate ID(s):: OSTI ID: 2419566
OSTI ID: 1962255

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 17 Vol. 62; ISSN 1433-7851

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

References (109)

Unconventional Nanofabrication for Supramolecular Electronics Yao, Yifan; Zhang, Lei; Orgiu, Emanuele Advanced Materials, Vol. 31, Issue 23 https://doi.org/10.1002/adma.201900599	journal	April 2019
Supramolecular Energy Materials Dumele, Oliver; Chen, Jiahao; Passarelli, James V. Advanced Materials, Vol. 32, Issue 17 https://doi.org/10.1002/adma.201907247	journal	March 2020
High Photocatalytic Oxygen Evolution via Strong Built‐In Electric Field Induced by High Crystallinity of Perylene Imide Supramolecule Sheng, Yuqiang; Li, Wenlu; Xu, Liangliang Advanced Materials, Vol. 34, Issue 10 https://doi.org/10.1002/adma.202102354	journal	January 2022
Practical Syntheses of Terrylene Chromophores from Naphthalene and Perylene Building Blocks Uersfeld, Daniel; Stappert, Sebastian; Li, Chen Advanced Synthesis & Catalysis, Vol. 359, Issue 23 https://doi.org/10.1002/adsc.201701003	journal	October 2017
Small Size, Big Impact: Recent Progress in Bottom‐Up Synthesized Nanographenes for Optoelectronic and Energy Applications Liu, Zhaoyang; Fu, Shuai; Liu, Xiaomin Advanced Science, Vol. 9, Issue 19 https://doi.org/10.1002/advs.202106055	journal	February 2022
Exciton Transport in Molecular Aggregates - From Natural Antennas to Synthetic Chromophore Systems Brixner, Tobias; Hildner, Richard; Köhler, Jürgen Advanced Energy Materials, Vol. 7, Issue 16 https://doi.org/10.1002/aenm.201700236	journal	July 2017
Wechselwirkungen mit aromatischen Ringen in chemischen und biologischen Erkennungsprozessen Meyer, Emmanuel A.; Castellano, Ronald K.; Diederich, François Angewandte Chemie, Vol. 115, Issue 11 https://doi.org/10.1002/ange.200390290	journal	March 2003
Selbstorganisierte Gelbildner für die organische Elektronik Babu, Sukumaran Santhosh; Prasanthkumar, Seelam; Ajayaghosh, Ayyappanpillai Angewandte Chemie, Vol. 124, Issue 8 https://doi.org/10.1002/ange.201106767	journal	January 2012
An Electron-Poor C₆₄ Nanographene by Palladium-Catalyzed Cascade C−C Bond Formation: One-Pot Synthesis and Single-Crystal Structure Analysis Seifert, Sabine; Shoyama, Kazutaka; Schmidt, David Angewandte Chemie, Vol. 128, Issue 22 https://doi.org/10.1002/ange.201601433	journal	April 2016
Base-Selective Five- versus Six-Membered Ring Annulation in Palladium-Catalyzed C-C Coupling Cascade Reactions: New Access to Electron-Poor Polycyclic Aromatic Dicarboximides Seifert, Sabine; Schmidt, David; Shoyama, Kazutaka Angewandte Chemie, Vol. 129, Issue 26 https://doi.org/10.1002/ange.201702889	journal	May 2017
Noncovalent Interactions of π Systems with Sulfur: The Atomic Chameleon of Molecular Recognition Motherwell, William B.; Moreno, Rafael B.; Pavlakos, Ilias Angewandte Chemie, Vol. 130, Issue 5 https://doi.org/10.1002/ange.201708485	journal	December 2017
Revision komplexer supramolekularer Polymerisation unter kinetischer und thermodynamischer Kontrolle Matern, Jonas; Dorca, Yeray; Sánchez, Luis Angewandte Chemie, Vol. 131, Issue 47 https://doi.org/10.1002/ange.201905724	journal	November 2019
O‐Doped Nanographenes: A Pyrano/Pyrylium Route Towards Semiconducting Cationic Mixed‐Valence Complexes Ðorđević, Luka; Valentini, Cataldo; Demitri, Nicola Angewandte Chemie, Vol. 132, Issue 10 https://doi.org/10.1002/ange.201914025	journal	January 2020
Quinoidal Azaacenes: 99 % Diradical Character Intorp, Sebastian N.; Hodecker, Manuel; Müller, Matthias Angewandte Chemie, Vol. 132, Issue 30 https://doi.org/10.1002/ange.201915977	journal	April 2020
Doubling the Length of the Longest Pyrene‐Pyrazinoquinoxaline Molecular Nanoribbons Hernández‐Culebras, Félix; Melle‐Franco, Manuel; Mateo‐Alonso, Aurelio Angewandte Chemie, Vol. 134, Issue 27 https://doi.org/10.1002/ange.202205018	journal	May 2022
Interactions with Aromatic Rings in Chemical and Biological Recognition Meyer, Emmanuel A.; Castellano, Ronald K.; Diederich, François Angewandte Chemie International Edition, Vol. 42, Issue 11 https://doi.org/10.1002/anie.200390319	journal	March 2003
Self-Assembled Gelators for Organic Electronics Babu, Sukumaran Santhosh; Prasanthkumar, Seelam; Ajayaghosh, Ayyappanpillai Angewandte Chemie International Edition, Vol. 51, Issue 8 https://doi.org/10.1002/anie.201106767	journal	January 2012
An Electron-Poor C ₆₄ Nanographene by Palladium-Catalyzed Cascade C−C Bond Formation: One-Pot Synthesis and Single-Crystal Structure Analysis Seifert, Sabine; Shoyama, Kazutaka; Schmidt, David Angewandte Chemie International Edition, Vol. 55, Issue 22 https://doi.org/10.1002/anie.201601433	journal	April 2016
Base-Selective Five- versus Six-Membered Ring Annulation in Palladium-Catalyzed C-C Coupling Cascade Reactions: New Access to Electron-Poor Polycyclic Aromatic Dicarboximides Seifert, Sabine; Schmidt, David; Shoyama, Kazutaka Angewandte Chemie International Edition, Vol. 56, Issue 26 https://doi.org/10.1002/anie.201702889	journal	May 2017
Noncovalent Interactions of π Systems with Sulfur: The Atomic Chameleon of Molecular Recognition Motherwell, William B.; Moreno, Rafael B.; Pavlakos, Ilias Angewandte Chemie International Edition, Vol. 57, Issue 5 https://doi.org/10.1002/anie.201708485	journal	December 2017
Revising Complex Supramolecular Polymerization under Kinetic and Thermodynamic Control Matern, Jonas; Dorca, Yeray; Sánchez, Luis Angewandte Chemie International Edition, Vol. 58, Issue 47 https://doi.org/10.1002/anie.201905724	journal	November 2019
O‐Doped Nanographenes: A Pyrano/Pyrylium Route Towards Semiconducting Cationic Mixed‐Valence Complexes Ðorđević, Luka; Valentini, Cataldo; Demitri, Nicola Angewandte Chemie International Edition, Vol. 59, Issue 10 https://doi.org/10.1002/anie.201914025	journal	January 2020
Quinoidal Azaacenes: 99 % Diradical Character Intorp, Sebastian N.; Hodecker, Manuel; Müller, Matthias Angewandte Chemie International Edition, Vol. 59, Issue 30 https://doi.org/10.1002/anie.201915977	journal	April 2020
Doubling the Length of the Longest Pyrene‐Pyrazinoquinoxaline Molecular Nanoribbons Hernández‐Culebras, Félix; Melle‐Franco, Manuel; Mateo‐Alonso, Aurelio Angewandte Chemie International Edition, Vol. 61, Issue 27 https://doi.org/10.1002/anie.202205018	journal	May 2022
Photoluminescence and Conductivity of Self-Assembled π–π Stacks of Perylene Bisimide Dyes Chen, Zhijian; Stepanenko, Vladimir; Dehm, Volker Chemistry - A European Journal, Vol. 13, Issue 2 https://doi.org/10.1002/chem.200600889	journal	January 2007
Controlling Photoconductivity in PBI Films by Supramolecular Assembly Draper, Emily R.; Archibald, Lewis J.; Nolan, Michael C. Chemistry - A European Journal, Vol. 24, Issue 16 https://doi.org/10.1002/chem.201800201	journal	February 2018
Tetrachlorinated Polycyclic Aromatic Dicarboximides: New Electron-Poor π-Scaffolds and NIR Emitters by Palladium-Catalyzed Annulation Reaction Mahl, Magnus; Shoyama, Kazutaka; Rühe, Jessica Chemistry - A European Journal, Vol. 24, Issue 37 https://doi.org/10.1002/chem.201801191	journal	June 2018
Long‐Lived Photocharges in Supramolecular Polymers of Low‐Band‐Gap Chromophores Hafner, Regina J.; Görl, Daniel; Sienkiewicz, Andrzej Chemistry – A European Journal, Vol. 26, Issue 43 https://doi.org/10.1002/chem.201904561	journal	July 2020
Self‐Assembly Propensity Dictates Lifetimes in Transient Naphthalimide–Dipeptide Nanofibers Kumar, Mohit; Sementa, Deborah; Narang, Vishal Chemistry – A European Journal, Vol. 26, Issue 38 https://doi.org/10.1002/chem.202001008	journal	June 2020
Supramolecular Polymers – we've Come Full Circle Aida, Takuzo; Meijer, E. W. Israel Journal of Chemistry, Vol. 60, Issue 1-2 https://doi.org/10.1002/ijch.201900165	journal	January 2020
Self‐Assembly of Bowl‐Shaped Naphthalimide‐Annulated Corannulene Renner, Rebecca; Stolte, Matthias; Würthner, Frank ChemistryOpen, Vol. 9, Issue 1 https://doi.org/10.1002/open.201900291	journal	November 2019
3D Printing of Supramolecular Polymer Hydrogels with Hierarchical Structure Sather, Nicholas A.; Sai, Hiroaki; Sasselli, Ivan R. Small, Vol. 17, Issue 5 https://doi.org/10.1002/smll.202005743	journal	January 2021
Chalcogen-bond driven molecular recognition at work Biot, Nicolas; Bonifazi, Davide Coordination Chemistry Reviews, Vol. 413 https://doi.org/10.1016/j.ccr.2020.213243	journal	June 2020
pH-Directed Aggregation to Control Photoconductivity in Self-Assembled Perylene Bisimides Draper, Emily R.; Greeves, Benjamin J.; Barrow, Michael Chem, Vol. 2, Issue 5 https://doi.org/10.1016/j.chempr.2017.03.022	journal	May 2017
Molecular Control of Internal Crystallization and Photocatalytic Function in Supramolecular Nanostructures Kazantsev, Roman V.; Dannenhoffer, Adam J.; Aytun, Taner Chem, Vol. 4, Issue 7 https://doi.org/10.1016/j.chempr.2018.04.002	journal	July 2018
Metallurgical alloy approach to two-dimensional supramolecular materials Dannenhoffer, Adam; Sai, Hiroaki; Bruckner, Eric P. Chem, Vol. 9, Issue 1 https://doi.org/10.1016/j.chempr.2022.09.026	journal	January 2023
Construction of rylene near-infrared absorption dyes with azaperylene monoimide Zhao, Xiaohong; Chen, Xuanwen; Yuan, Zhongyi Dyes and Pigments, Vol. 173 https://doi.org/10.1016/j.dyepig.2019.107930	journal	February 2020
New directions in supramolecular electronics Jain, Ankit; George, Subi J. Materials Today, Vol. 18, Issue 4 https://doi.org/10.1016/j.mattod.2015.01.015	journal	May 2015
Supramolecular Polymerization: A Conceptual Expansion for Innovative Materials Hashim, P. K.; Bergueiro, Julian; Meijer, E. W. Progress in Polymer Science, Vol. 105 https://doi.org/10.1016/j.progpolymsci.2020.101250	journal	June 2020
Template-Directed Synthesis of Molecular Nanorings and Cages Bols, Pernille S.; Anderson, Harry L. Accounts of Chemical Research, Vol. 51, Issue 9 https://doi.org/10.1021/acs.accounts.8b00313	journal	August 2018
N-Heteroacenes and N-Heteroarenes as N-Nanocarbon Segments Bunz, Uwe H. F.; Freudenberg, Jan Accounts of Chemical Research, Vol. 52, Issue 6 https://doi.org/10.1021/acs.accounts.9b00160	journal	June 2019
Noncovalent Aqua Materials Based on Perylene Diimides Krieg, Elisha; Niazov-Elkan, Angelica; Cohen, Erez Accounts of Chemical Research, Vol. 52, Issue 9 https://doi.org/10.1021/acs.accounts.9b00188	journal	August 2019
Heteroatom-Doped Nanographenes with Structural Precision Wang, Xiao-Ye; Yao, Xuelin; Narita, Akimitsu Accounts of Chemical Research, Vol. 52, Issue 9 https://doi.org/10.1021/acs.accounts.9b00322	journal	August 2019
Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds Borissov, Arseni; Maurya, Yogesh Kumar; Moshniaha, Liliia Chemical Reviews, Vol. 122, Issue 1 https://doi.org/10.1021/acs.chemrev.1c00449	journal	December 2021
Self-Assembly of Perylene Imide Molecules into 1D Nanostructures: Methods, Morphologies, and Applications Chen, Shuai; Slattum, Paul; Wang, Chuanyi Chemical Reviews, Vol. 115, Issue 21 https://doi.org/10.1021/acs.chemrev.5b00312	journal	October 2015
Supramolecular Polymers in Aqueous Media Krieg, Elisha; Bastings, Maartje M. C.; Besenius, Pol Chemical Reviews, Vol. 116, Issue 4 https://doi.org/10.1021/acs.chemrev.5b00369	journal	January 2016
Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications Stępień, Marcin; Gońka, Elżbieta; Żyła, Marika Chemical Reviews, Vol. 117, Issue 4 https://doi.org/10.1021/acs.chemrev.6b00076	journal	June 2016
Structurally Constrained Boron-, Nitrogen-, Silicon-, and Phosphorus-Centered Polycyclic π-Conjugated Systems Hirai, Masato; Tanaka, Naoki; Sakai, Mika Chemical Reviews, Vol. 119, Issue 14 https://doi.org/10.1021/acs.chemrev.8b00637	journal	March 2019
A General Synthetic Route to Polycyclic Aromatic Dicarboximides by Palladium-Catalyzed Annulation Reaction Shoyama, Kazutaka; Mahl, Magnus; Seifert, Sabine The Journal of Organic Chemistry, Vol. 83, Issue 10 https://doi.org/10.1021/acs.joc.8b00301	journal	March 2018
Palladium-Catalyzed [3+2] Annulation of Naphthalimide Acceptors and Thiophene Donors Shoyama, Kazutaka; Mahl, Magnus; Niyas, M. A. The Journal of Organic Chemistry, Vol. 85, Issue 1 https://doi.org/10.1021/acs.joc.9b02372	journal	November 2019
Controlling Visible Light Driven Photoconductivity in Self-Assembled Perylene Bisimide Structures Walsh, James J.; Lee, Jonathan R.; Draper, Emily R. The Journal of Physical Chemistry C, Vol. 120, Issue 33 https://doi.org/10.1021/acs.jpcc.6b06222	journal	August 2016
Molecular Packing of Amphiphilic Nanosheets Resolved by X-ray Scattering Harutyunyan, Boris; Dannenhoffer, Adam; Kewalramani, Sumit The Journal of Physical Chemistry C, Vol. 121, Issue 2 https://doi.org/10.1021/acs.jpcc.6b11391	journal	January 2017
Controlling the Assembly and Properties of Low-Molecular-Weight Hydrogelators Draper, Emily R.; Adams, Dave J. Langmuir, Vol. 35, Issue 20 https://doi.org/10.1021/acs.langmuir.9b00716	journal	April 2019
Imaging Supramolecular Morphogenesis with Confocal Laser Scanning Microscopy at Elevated Temperatures Sai, Hiroaki; Lau, Garrett C.; Dannenhoffer, Adam J. Nano Letters, Vol. 20, Issue 6 https://doi.org/10.1021/acs.nanolett.0c00662	journal	May 2020
Growth of Extra-Large Chromophore Supramolecular Polymers for Enhanced Hydrogen Production Dannenhoffer, Adam J.; Sai, Hiroaki; Harutyunyan, Boris Nano Letters, Vol. 21, Issue 9 https://doi.org/10.1021/acs.nanolett.0c05024	journal	April 2021
O-Annulation to Polycyclic Aromatic Hydrocarbons: A Tale of Optoelectronic Properties from Five- to Seven-Membered Rings Đorđević, Luka; Milano, Domenico; Demitri, Nicola Organic Letters, Vol. 22, Issue 11 https://doi.org/10.1021/acs.orglett.0c01331	journal	May 2020
Electron-Poor Bowl-Shaped Polycyclic Aromatic Dicarboximides: Synthesis, Crystal Structures, and Optical and Redox Properties Shoyama, Kazutaka; Schmidt, David; Mahl, Magnus Organic Letters, Vol. 19, Issue 19 https://doi.org/10.1021/acs.orglett.7b02618	journal	September 2017
Effect of Core Oligomer Length on the Phase Behavior and Assembly of π-Conjugated Peptides Jira, Edward R.; Shmilovich, Kirill; Kale, Tejaswini S. ACS Applied Materials & Interfaces, Vol. 12, Issue 18 https://doi.org/10.1021/acsami.0c02095	journal	April 2020
Dynamic Peptide Library for the Discovery of Charge Transfer Hydrogels Berdugo, Cristina; Nalluri, Siva Krishna Mohan; Javid, Nadeem ACS Applied Materials & Interfaces, Vol. 7, Issue 46 https://doi.org/10.1021/acsami.5b08968	journal	November 2015
Tuning Supramolecular Structure and Functions of Peptide bola -Amphiphile by Solvent Evaporation–Dissolution Wang, Anhe; Cui, Lingyun; Debnath, Sisir ACS Applied Materials & Interfaces, Vol. 9, Issue 25 https://doi.org/10.1021/acsami.7b05661	journal	June 2017
Hybrid Nanocrystals of Small Molecules and Chemically Disordered Polymers Bruckner, Eric P.; Curk, Tine; Đorđević, Luka ACS Nano, Vol. 16, Issue 6 https://doi.org/10.1021/acsnano.2c00266	journal	May 2022
Directed Assembly of Nanomaterials for Making Nanoscale Devices and Structures: Mechanisms and Applications Chai, Zhimin; Childress, Anthony; Busnaina, Ahmed A. ACS Nano, Vol. 16, Issue 11 https://doi.org/10.1021/acsnano.2c07910	journal	October 2022
Supramolecular Construction of Optoelectronic Biomaterials Tovar, John D. Accounts of Chemical Research, Vol. 46, Issue 7 https://doi.org/10.1021/ar3002969	journal	March 2013
Chlorophyll J-Aggregates: From Bioinspired Dye Stacks to Nanotubes, Liquid Crystals, and Biosupramolecular Electronics Sengupta, Sanchita; Würthner, Frank Accounts of Chemical Research, Vol. 46, Issue 11 https://doi.org/10.1021/ar400017u	journal	July 2013
Self-Assembly Strategies for Integrating Light Harvesting and Charge Separation in Artificial Photosynthetic Systems Wasielewski, Michael R. Accounts of Chemical Research, Vol. 42, Issue 12 https://doi.org/10.1021/ar9001735	journal	December 2009
Semiconducting Single Crystals Comprising Segregated Arrays of Complexes of C ₆₀ Barnes, Jonathan C.; Dale, Edward J.; Prokofjevs, Aleksandrs Journal of the American Chemical Society, Vol. 137, Issue 6 https://doi.org/10.1021/ja512959g	journal	February 2015
Long-Lived Charge-Transfer State from B–N Frustrated Lewis Pairs Enchained in Supramolecular Copolymers Adelizzi, Beatrice; Chidchob, Pongphak; Tanaka, Naoki Journal of the American Chemical Society, Vol. 142, Issue 39 https://doi.org/10.1021/jacs.0c06921	journal	September 2020
Photocatalytic Aqueous CO₂ Reduction to CO and CH₄ Sensitized by Ullazine Supramolecular Polymers Dumele, Oliver; Đorđević, Luka; Sai, Hiroaki Journal of the American Chemical Society, Vol. 144, Issue 7 https://doi.org/10.1021/jacs.1c12155	journal	February 2022
Fluorescence Enhancement by Supramolecular Sequestration of a C₅₄-Nanographene Trisimide by Hexabenzocoronene Pigulski, Bartłomiej; Shoyama, Kazutaka; Sun, Meng-Jia Journal of the American Chemical Society, Vol. 144, Issue 13 https://doi.org/10.1021/jacs.2c00142	journal	March 2022
Helically Twisted Nanoribbons Based on Emissive Near-Infrared Responsive Quaterrylene Bisimides Mahlmeister, Bernhard; Mahl, Magnus; Reichelt, Helmut Journal of the American Chemical Society, Vol. 144, Issue 23 https://doi.org/10.1021/jacs.2c02947	journal	June 2022
Molecular Carbon Imides Jiang, Wei; Wang, Zhaohui Journal of the American Chemical Society, Vol. 144, Issue 33 https://doi.org/10.1021/jacs.2c04642	journal	July 2022
Supramolecular Packing Controls H ₂ Photocatalysis in Chromophore Amphiphile Hydrogels Weingarten, Adam S.; Kazantsev, Roman V.; Palmer, Liam C. Journal of the American Chemical Society, Vol. 137, Issue 48 https://doi.org/10.1021/jacs.5b10027	journal	November 2015
Extended-Charge-Transfer Excitons in Crystalline Supramolecular Photocatalytic Scaffolds Hestand, Nicholas J.; Kazantsev, Roman V.; Weingarten, Adam S. Journal of the American Chemical Society, Vol. 138, Issue 36 https://doi.org/10.1021/jacs.6b05673	journal	September 2016
Crystal-Phase Transitions and Photocatalysis in Supramolecular Scaffolds Kazantsev, Roman V.; Dannenhoffer, Adam J.; Weingarten, Adam S. Journal of the American Chemical Society, Vol. 139, Issue 17 https://doi.org/10.1021/jacs.6b13156	journal	April 2017
Supramolecular Self-Assembly in a Sub-micrometer Electrodic Cavity: Fabrication of Heat-Reversible π-Gel Memristor Zhang, Lei; Li, Songlin; Squillaci, Marco A. Journal of the American Chemical Society, Vol. 139, Issue 41 https://doi.org/10.1021/jacs.7b04347	journal	September 2017
Chromophore Dipole Directs Morphology and Photocatalytic Hydrogen Generation Weingarten, Adam S.; Dannenhoffer, Adam J.; Kazantsev, Roman V. Journal of the American Chemical Society, Vol. 140, Issue 15 https://doi.org/10.1021/jacs.7b12641	journal	April 2018
Synthesis of a Carbon Nanocone by Cascade Annulation Shoyama, Kazutaka; Würthner, Frank Journal of the American Chemical Society, Vol. 141, Issue 33 https://doi.org/10.1021/jacs.9b06617	journal	August 2019
Inserting Nitrogen: An Effective Concept To Create Nonplanar and Stimuli-Responsive Perylene Bisimide Analogues Hayakawa, Sakiho; Kawasaki, Ayumi; Hong, Yongseok Journal of the American Chemical Society, Vol. 141, Issue 50 https://doi.org/10.1021/jacs.9b09556	journal	November 2019
Bent-Shaped p -Type Small-Molecule Organic Semiconductors: A Molecular Design Strategy for Next-Generation Practical Applications Okamoto, Toshihiro; Yu, Craig P.; Mitsui, Chikahiko Journal of the American Chemical Society, Vol. 142, Issue 20 https://doi.org/10.1021/jacs.9b10450	journal	April 2020
Molecule Isomerism Modulates the Diradical Properties of Stable Singlet Diradicaloids Barker, Joshua E.; Dressler, Justin J.; Cárdenas Valdivia, Abel Journal of the American Chemical Society, Vol. 142, Issue 3 https://doi.org/10.1021/jacs.9b11898	journal	December 2019
A Deep Blue B,N-Doped Heptacene Emitter That Shows Both Thermally Activated Delayed Fluorescence and Delayed Fluorescence by Triplet–Triplet Annihilation Suresh, Subeesh Madayanad; Duda, Eimantas; Hall, David Journal of the American Chemical Society, Vol. 142, Issue 14 https://doi.org/10.1021/jacs.9b13704	journal	March 2020
Perylenediimide Nanowires and Their Use in Fabricating Field-Effect Transistors and Complementary Inverters Briseno, Alejandro L.; Mannsfeld, Stefan C. B.; Reese, Colin Nano Letters, Vol. 7, Issue 9, p. 2847-2853 https://doi.org/10.1021/nl071495u	journal	September 2007
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
Non-equilibrium steady states in supramolecular polymerization Sorrenti, Alessandro; Leira-Iglesias, Jorge; Sato, Akihiro Nature Communications, Vol. 8, Issue 1 https://doi.org/10.1038/ncomms15899	journal	June 2017
Supramolecular block copolymers by kinetically controlled co-self-assembly of planar and core-twisted perylene bisimides Görl, Daniel; Zhang, Xin; Stepanenko, Vladimir Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms8009	journal	May 2015
Towards high charge-carrier mobilities by rational design of the shape and periphery of discotics Feng, Xinliang; Marcon, Valentina; Pisula, Wojciech Nature Materials, Vol. 8, Issue 5 https://doi.org/10.1038/nmat2427	journal	April 2009
Combining high-resolution scanning tunnelling microscopy and first-principles simulations to identify halogen bonding Lawrence, James; Sosso, Gabriele C.; Đorđević, Luka Nature Communications, Vol. 11, Issue 1 https://doi.org/10.1038/s41467-020-15898-2	journal	April 2020
Amino-acid-encoded biocatalytic self-assembly enables the formation of transient conducting nanostructures Kumar, Mohit; Ing, Nicole L.; Narang, Vishal Nature Chemistry, Vol. 10, Issue 7 https://doi.org/10.1038/s41557-018-0047-2	journal	April 2018
Multilayer stacks of polycyclic aromatic hydrocarbons Mahl, Magnus; Niyas, M. A.; Shoyama, Kazutaka Nature Chemistry, Vol. 14, Issue 4 https://doi.org/10.1038/s41557-021-00861-5	journal	February 2022
Supramolecular polymerization through kinetic pathway control and living chain growth Wehner, Marius; Würthner, Frank Nature Reviews Chemistry, Vol. 4, Issue 1 https://doi.org/10.1038/s41570-019-0153-8	journal	December 2019
Shaping and structuring supramolecular gels Chivers, Phillip R. A.; Smith, David K. Nature Reviews Materials, Vol. 4, Issue 7 https://doi.org/10.1038/s41578-019-0111-6	journal	May 2019
Elucidating the nanoscale origins of organic electronic function by conductive atomic force microscopy Mativetsky, Jeffrey M.; Loo, Yueh-Lin; Samorì, Paolo J. Mater. Chem. C, Vol. 2, Issue 17 https://doi.org/10.1039/C3TC32050B	journal	January 2014
Water-soluble perylenediimides: design concepts and biological applications Sun, Mengmeng; Müllen, Klaus; Yin, Meizhen Chemical Society Reviews, Vol. 45, Issue 6 https://doi.org/10.1039/C5CS00754B	journal	January 2016
Self-assembly, self-sorting, and electronic properties of a diketopyrrolopyrrole hydrogelator Draper, Emily R.; Dietrich, Bart; Adams, Dave J. Chemical Communications, Vol. 53, Issue 11 https://doi.org/10.1039/C6CC10083J	journal	January 2017
A cross-coupling-annulation cascade from peri-dibromonaphthalimide to pseudo-rylene bisimides Seifert, Sabine; Schmidt, David; Würthner, Frank Organic Chemistry Frontiers, Vol. 3, Issue 11 https://doi.org/10.1039/C6QO00421K	journal	January 2016
Self-sorted photoconductive xerogels Draper, Emily R.; Lee, Jonathan R.; Wallace, Matthew Chemical Science, Vol. 7, Issue 10 https://doi.org/10.1039/C6SC02644C	journal	January 2016
Non-equilibrium supramolecular polymerization Sorrenti, Alessandro; Leira-Iglesias, Jorge; Markvoort, Albert J. Chemical Society Reviews, Vol. 46, Issue 18 https://doi.org/10.1039/C7CS00121E	journal	January 2017
Carbocyclization approaches to electron-deficient nanographenes and their analogues Zhylitskaya, Halina; Stępień, Marcin Organic Chemistry Frontiers, Vol. 5, Issue 15 https://doi.org/10.1039/C8QO00423D	journal	January 2018
Impact of charge switching stimuli on supramolecular perylene monoimide assemblies Dannenhoffer, Adam; Sai, Hiroaki; Huang, Dongxu Chemical Science, Vol. 10, Issue 22 https://doi.org/10.1039/C8SC05595E	journal	January 2019
Selenoamides modulate dipole–dipole interactions in hydrogen bonded supramolecular polymers of 1,3,5-substituted benzenes Berrocal, José Augusto; Mabesoone, Mathijs F. J.; García Iglesias, Miguel Chemical Communications, Vol. 55, Issue 99 https://doi.org/10.1039/C9CC08423A	journal	January 2019
Visible-light photooxidation in water by ¹ O ₂ -generating supramolecular hydrogels Biswas, Sankarsan; Kumar, Mohit; Levine, Andrew M. Chemical Science, Vol. 11, Issue 16 https://doi.org/10.1039/C9SC06481H	journal	January 2020
Controlled supramolecular polymerization of π-systems Ghosh, Goutam; Dey, Pradip; Ghosh, Suhrit Chemical Communications, Vol. 56, Issue 50 https://doi.org/10.1039/D0CC02787A	journal	January 2020
Synthesis of polycyclic aromatic hydrocarbons by palladium-catalysed [3 + 3] annulation Pigulski, Bartłomiej; Ximenis, Marta; Shoyama, Kazutaka Organic Chemistry Frontiers, Vol. 7, Issue 19 https://doi.org/10.1039/D0QO00968G	journal	January 2020
Molecular nanoribbon gels Martínez-Abadía, Marta; Dubey, Rajeev K.; Fernández, Mercedes Chemical Science, Vol. 13, Issue 36 https://doi.org/10.1039/D2SC02637F	journal	January 2022
Supramolecular control of self-assembling terthiophene–peptide conjugates through the amino acid side chain Lehrman, Jessica A.; Cui, Honggang; Tsai, Wei-Wen Chemical Communications, Vol. 48, Issue 78 https://doi.org/10.1039/c2cc34375d	journal	January 2012
Supramolecular self-assemblies as functional nanomaterials Busseron, Eric; Ruff, Yves; Moulin, Emilie Nanoscale, Vol. 5, Issue 16 https://doi.org/10.1039/c3nr02176a	journal	January 2013
Functional Supramolecular Polymers Aida, T.; Meijer, E. W.; Stupp, S. I. Science, Vol. 335, Issue 6070 https://doi.org/10.1126/science.1205962	journal	February 2012
Supramolecular Chemistry: Receptors, Catalysts, and Carriers Lehn, J. -M. Science, Vol. 227, Issue 4689 https://doi.org/10.1126/science.227.4689.849	journal	February 1985
Globular Aggregates Stemming from the Self-Assembly of an Amphiphilic N-Annulated Perylene Bisimide in Aqueous Media Martínez, Manuel A.; Greciano, Elisa E.; Cuéllar, Jorge Nanomaterials, Vol. 11, Issue 6 https://doi.org/10.3390/nano11061457	journal	May 2021

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