Solid-Phase Synthesis of Self-Assembling Multivalent π-Conjugated Peptides

Sanders, Allix M.; Kale, Tejaswini S.; Katz, Howard E.; Tovar, John D.

doi:10.1021/acsomega.6b00414

Title: Solid-Phase Synthesis of Self-Assembling Multivalent π-Conjugated Peptides

Journal Article · Mon Feb 06 19:00:00 EST 2017 · ACS Omega

DOI: https://doi.org/10.1021/acsomega.6b00414 · OSTI ID:1342800

Sanders, Allix M. ^[1]; Kale, Tejaswini S. ^[1];

^[1];

^[1]

Department of Chemistry, Krieger School of Arts and Sciences, ‡Department of Materials Science and Engineering, Whiting School of Engineering, §Institute of NanoBioTechnology, Johns Hopkins University, 3400 N. Charles Street, Baltimore, Maryland 21218, United States

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Research Organization:: John Hopkins Univ., Baltimore, MD (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: SC0004857

OSTI ID:: 1342800

Journal Information:: ACS Omega, Journal Name: ACS Omega Journal Issue: 2 Vol. 2; ISSN 2470-1343

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (55)

Chiral Perylene Bisimide–Melamine Assemblies: Hydrogen Bond-Directed Growth of Helically Stacked Dyes with Chiroptical Properties Thalacker, C.; Würthner, F. Advanced Functional Materials, Vol. 12, Issue 3 https://doi.org/10.1002/1616-3028(200203)12:3<209::AID-ADFM209>3.0.CO;2-Y	journal	March 2002
4,4?,4?-Tris(stearoylamino)triphenylamine as a novel material for functional molecular gels Yasuda, Yoshiaki; Takebe, Yasuo; Fukumoto, Masahiro Advanced Materials, Vol. 8, Issue 9 https://doi.org/10.1002/adma.19960080907	journal	September 1996
Planarized Star-Shaped Oligothiophenes as a New Class of Organic Semiconductors for Heterojunction Solar Cells de Bettignies, R.; Nicolas, Y.; Blanchard, P. Advanced Materials, Vol. 15, Issue 22 https://doi.org/10.1002/adma.200305168	journal	November 2003
Aligned Macroscopic Domains of Optoelectronic Nanostructures Prepared via Shear-Flow Assembly of Peptide Hydrogels Wall, Brian D.; Diegelmann, Stephen R.; Zhang, Shuming Advanced Materials, Vol. 23, Issue 43, p. 5009-5014 https://doi.org/10.1002/adma.201102963	journal	October 2011
Sergeants-and-Soldiers Principle in Chiral Columnar Stacks of Disc-Shaped Molecules withC3 Symmetry Palmans, Anja R. A.; Vekemans, Jef A. J. M.; Havinga, Edsko E. Angewandte Chemie International Edition in English, Vol. 36, Issue 23 https://doi.org/10.1002/anie.199726481	journal	December 1997
Self-Assembling Decacyclene Triimides Prepared through a Regioselective Hextuple Friedel-Crafts Carbamylation Pho, Toan V.; Toma, Francesca M.; Chabinyc, Michael L. Angewandte Chemie International Edition, Vol. 52, Issue 5, p. 1446-1451 https://doi.org/10.1002/anie.201207608	journal	December 2012
pH-Switchable Ampholytic Supramolecular Copolymers Frisch, Hendrik; Unsleber, Jan Patrick; Lüdeker, David Angewandte Chemie International Edition, Vol. 52, Issue 38 https://doi.org/10.1002/anie.201303810	journal	August 2013
Extended-Core Discotic Liquid Crystals Based on the Intramolecular H-Bonding in N -Acylated 2,2′-Bipyridine-3,3′-diamine Moieties Palmans, Anja R. A.; Vekemans, Jozef A. J. M.; Fischer, Hartmut Chemistry - A European Journal, Vol. 3, Issue 2 https://doi.org/10.1002/chem.19970030220	journal	February 1997
Tuning the Stacking Properties ofC3-Symmetrical Molecules by Modifying a Dipeptide Motif van den Hout, Kelly P.; Martín-Rapún, Rafael; Vekemans, Jef A. J. M. Chemistry - A European Journal, Vol. 13, Issue 29 https://doi.org/10.1002/chem.200700630	journal	October 2007
Asymmetrically Substituted Benzene-1,3,5-tricarboxamides: Self-Assembly and Odd-Even Effects in the Solid State and in Dilute Solution Stals, Patrick J. M.; Smulders, Maarten M. J.; Martín-Rapún, Rafael Chemistry - A European Journal, Vol. 15, Issue 9 https://doi.org/10.1002/chem.200802196	journal	February 2009
Dynamic Supramolecular Polymers Based on Benzene-1,3,5-tricarboxamides: The Influence of Amide Connectivity on Aggregate Stability and Amplification of Chirality Stals, Patrick J. M.; Everts, Jeffrey C.; de Bruijn, Robin Chemistry - A European Journal, Vol. 16, Issue 3 https://doi.org/10.1002/chem.200902635	journal	December 2009
Controlled Supramolecular Oligomerization of C3-Symmetrical Molecules in Water: The Impact of Hydrophobic Shielding Besenius, Pol; van den Hout, Kelly P.; Albers, Harald M. H. G. Chemistry - A European Journal, Vol. 17, Issue 18 https://doi.org/10.1002/chem.201002976	journal	March 2011
Surface Active Peptide-Mediated Porphyrin Aggregation Venkatesh, B.; Jayakumar, R.; Pandian, R. P. Biochemical and Biophysical Research Communications, Vol. 223, Issue 2 https://doi.org/10.1006/bbrc.1996.0904	journal	June 1996
Liquid crystals II. The tail design via β-oxygen atom modification for the remarkably enhanced stability of hexakis (alkanoyloxy) triphenylene mesophase Tabushi, Iwao; Yamamura, Kazuo; Okada, Yukihiro Tetrahedron Letters, Vol. 28, Issue 20 https://doi.org/10.1016/S0040-4039(00)96098-2	journal	January 1987
Tetra-phenyl porphyrin based thin film transistors Checcoli, P.; Conte, G.; Salvatori, S. Synthetic Metals, Vol. 138, Issue 1-2 https://doi.org/10.1016/S0379-6779(02)01308-5	journal	June 2003
Organic field effect transistors based on 5,10,15,20-tetrakis(4-pentyloxyphenyl)porphyrin single crystal Ma, Pan; Chen, Yanli; Cai, Xue Synthetic Metals, Vol. 160, Issue 5-6 https://doi.org/10.1016/j.synthmet.2009.11.040	journal	March 2010
C3-Symmetric, amino acid based organogelators and thickeners: a systematic study of structure–property relations de Loos, Maaike; van Esch, Jan H.; Kellogg, Richard M. Tetrahedron, Vol. 63, Issue 31 https://doi.org/10.1016/j.tet.2007.02.066	journal	July 2007
H-Bond-Stabilized Triphenylene-Based Columnar Discotic Liquid Crystals Paraschiv, Ioan; Giesbers, Marcel; van Lagen, Barend Chemistry of Materials, Vol. 18, Issue 4 https://doi.org/10.1021/cm052221f	journal	February 2006
Meso-Substituted Porphyrins for Dye-Sensitized Solar Cells Urbani, Maxence; Grätzel, Michael; Nazeeruddin, Mohammad Khaja Chemical Reviews, Vol. 114, Issue 24 https://doi.org/10.1021/cr5001964	journal	November 2014
Dendrimer Porphyrins and Phthalocyanines Li, Wei-Shi; Aida, Takuzo Chemical Reviews, Vol. 109, Issue 11 https://doi.org/10.1021/cr900186c	journal	September 2009
Intramolecular photochemical electron transfer. 6. Bridge and solvent dependence of electron transfer in covalently linked porphyrin-peptide-quinone compounds Liu, Jing Yao; Schmidt, John A.; Bolton, James R. The Journal of Physical Chemistry, Vol. 95, Issue 18 https://doi.org/10.1021/j100171a035	journal	September 1991
Hierarchical Growth of Chiral Self-Assembled Structures in Protic Media ^† Brunsveld, L.; Zhang, H.; Glasbeek, M. Journal of the American Chemical Society, Vol. 122, Issue 26 https://doi.org/10.1021/ja0005237	journal	July 2000
Enforced Stacking in Crowded Arenes Bushey, Mark L.; Hwang, Austin; Stephens, Peter W. Journal of the American Chemical Society, Vol. 123, Issue 33 https://doi.org/10.1021/ja0104148	journal	August 2001
C ₃ -Symmetrical Supramolecular Architectures: Fibers and Organic Gels from Discotic Trisamides and Trisureas van Gorp, Judith J.; Vekemans, Jef A. J. M.; Meijer, E. W. Journal of the American Chemical Society, Vol. 124, Issue 49 https://doi.org/10.1021/ja020984n	journal	December 2002
Counterion-Dependent Excitonic Spectra of Tetra( p -carboxyphenyl)porphyrin Aggregates in Acidic Aqueous Solution Choi, Myong Yong; Pollard, Jennifer A.; Webb, M. Adam Journal of the American Chemical Society, Vol. 125, Issue 3 https://doi.org/10.1021/ja0274397	journal	January 2003
Probing the Interior of Peptide Amphiphile Supramolecular Aggregates Tovar, John D.; Claussen, Randal C.; Stupp, Samuel I. Journal of the American Chemical Society, Vol. 127, Issue 20 https://doi.org/10.1021/ja043764d	journal	May 2005
Artificial Peptide-Nanospheres Self-Assembled from Three-Way Junctions of β-Sheet-Forming Peptides Matsuura, Kazunori; Murasato, Kazuya; Kimizuka, Nobuo Journal of the American Chemical Society, Vol. 127, Issue 29 https://doi.org/10.1021/ja052644i	journal	July 2005
Self-Assembly of Peptide Porphyrin Complexes: Toward the Development of Smart Biomaterials Kovaric, Brian C.; Kokona, Bashkim; Schwab, Alexander D. Journal of the American Chemical Society, Vol. 128, Issue 13 https://doi.org/10.1021/ja056357q	journal	April 2006
Insight into the Mechanisms of Cooperative Self-Assembly: The “Sergeants-and-Soldiers” Principle of Chiral and Achiral C ₃ -Symmetrical Discotic Triamides Smulders, Maarten M. J.; Schenning, Albertus P. H. J.; Meijer, E. W. Journal of the American Chemical Society, Vol. 130, Issue 2 https://doi.org/10.1021/ja075987k	journal	January 2008
Two-Fold Odd–Even Effect in Self-Assembled Nanowires from Oligopeptide-Polymer-Substituted Perylene Bisimides Marty, Roman; Nigon, Robin; Leite, Deborah Journal of the American Chemical Society, Vol. 136, Issue 10 https://doi.org/10.1021/ja412384p	journal	February 2014
Liquid Crystals Obtained from Disclike Mesogenic Diacetylenes and Their Polymerization Chang, Ji Young; Baik, Jung Hyun; Lee, Chan Bong Journal of the American Chemical Society, Vol. 119, Issue 13 https://doi.org/10.1021/ja961193m	journal	April 1997
Synthesis, Characterization, and Metabolic Stability of Porphyrin−Peptide Conjugates Bearing Bifunctional Signaling Sequences Sibrian-Vazquez, Martha; Jensen, Timothy J.; Vicente, M. Graça H. Journal of Medicinal Chemistry, Vol. 51, Issue 10 https://doi.org/10.1021/jm701050j	journal	April 2008
Viscoelastic Behavior of Supramolecular Polymeric Systems Consisting of N , N ‘ , N ‘ ‘ -Tris(3,7-dimethyloctyl)benzene-1,3,5-tricarboxamide and n -Alkanes Shikata, Toshiyuki; Ogata, Daisuke; Hanabusa, Kenji The Journal of Physical Chemistry B, Vol. 108, Issue 2 https://doi.org/10.1021/jp030510q	journal	January 2004
Enhancement of Light-Energy Conversion Efficiency by Multi-Porphyrin Arrays of Porphyrin−Peptide Oligomers with Fullerene Clusters Hasobe, Taku; Kamat, Prashant V.; Troiani, Vincent The Journal of Physical Chemistry B, Vol. 109, Issue 1 https://doi.org/10.1021/jp045246v	journal	January 2005
Complementary π–π Interactions Induce Multicomponent Coassembly into Functional Fibrils Ryan, Derek M.; Doran, Todd M.; Nilsson, Bradley L. Langmuir, Vol. 27, Issue 17 https://doi.org/10.1021/la202070d	journal	September 2011
Supramolecular Polymorphism: Tunable Electronic Interactions within π-Conjugated Peptide Nanostructures Dictated by Primary Amino Acid Sequence Wall, Brian D.; Zacca, Ashley E.; Sanders, Allix M. Langmuir, Vol. 30, Issue 20 https://doi.org/10.1021/la500222y	journal	May 2014
Peptide-Based Supramolecular Semiconductor Nanomaterials via Pd-Catalyzed Solid-Phase “Dimerizations” Sanders, Allix M.; Dawidczyk, Thomas J.; Katz, Howard E. ACS Macro Letters, Vol. 1, Issue 11 https://doi.org/10.1021/mz3004665	journal	October 2012
Helical Growth of Semiconducting Columnar Dye Assemblies Based on Chiral Perylene Bisimides Dehm, Volker; Chen, Zhijian; Baumeister, Ute Organic Letters, Vol. 9, Issue 6 https://doi.org/10.1021/ol0700963	journal	March 2007
The influence of oligo(ethylene glycol) side chains on the self-assembly of benzene-1,3,5-tricarboxamides in the solid state and in solution Stals, Patrick J. M.; Haveman, Jan F.; Martín-Rapún, Rafael J. Mater. Chem., Vol. 19, Issue 1 https://doi.org/10.1039/B816418E	journal	January 2009
Sterically demanding benzene-1,3,5-tricarboxamides: tuning the mechanisms of supramolecular polymerization and chiral amplification Veld, Martijn A. J.; Haveman, Daniël; Palmans, Anja R. A. Soft Matter, Vol. 7, Issue 2 https://doi.org/10.1039/C0SM00516A	journal	January 2011
Formation of a supramolecular chromophore: a spectroscopic and theoretical study Bernet, Andreas; Albuquerque, Rodrigo Q.; Behr, Marina Soft Matter, Vol. 8, Issue 1 https://doi.org/10.1039/C1SM06789C	journal	January 2012
Synthesis and self-assembly of a C ₃ -symmetric benzene-1,3,5-tricarboxamide (BTA) anchored naphthalene diimide disc Narayan, Bhawani; Kulkarni, Chidambar; George, Subi J. J. Mater. Chem. C, Vol. 1, Issue 4 https://doi.org/10.1039/C2TC00742H	journal	January 2013
Energy transfer within responsive pi-conjugated coassembled peptide-based nanostructures in aqueous environments Ardoña, Herdeline Ann M.; Tovar, John D. Chemical Science, Vol. 6, Issue 2 https://doi.org/10.1039/C4SC03122A	journal	January 2015
Hydrogen-bonded porous solid derived from trimesic amide Palmans, Anja R. A.; Vekemans, Jef A. J. M.; Meijer, E. W. Chemical Communications, Issue 22 https://doi.org/10.1039/a705339h	journal	January 1997
The influence of hydrogen bonding and π–π stacking interactions on the self-assembly properties of C3-symmetrical oligo(p-phenylenevinylene) discs van Herrikhuyzen, Jeroen; Jonkheijm, Pascal; Schenning, Albertus P. H. J. Organic & Biomolecular Chemistry, Vol. 4, Issue 8 https://doi.org/10.1039/b517993a	journal	January 2006
Formation of triple helical nanofibers using self-assembling chiral benzene-1,3,5-tricarboxamides and reversal of the nanostructure's handedness using mirror image building blocks Bose, Partha Pratim; Drew, Michael G. B.; Das, Apurba K. Chemical Communications, Issue 30 https://doi.org/10.1039/b606371c	journal	January 2006
On-resin dimerization incorporates a diverse array of π-conjugated functionality within aqueous self-assembling peptide backbones Vadehra, Geeta S.; Wall, Brian D.; Diegelmann, Stephen R. Chemical Communications, Vol. 46, Issue 22 https://doi.org/10.1039/c0cc00301h	journal	January 2010
Self-assembling porphyrins and phthalocyanines for photoinduced charge separation and charge transport Imahori, Hiroshi; Umeyama, Tomokazu; Kurotobi, Kei Chemical Communications, Vol. 48, Issue 34 https://doi.org/10.1039/c2cc30621b	journal	January 2012
Structural modulation of internal charge transfer in small molecular donors for organic solar cells Leliège, Antoine; Régent, Charles-Henri Le; Allain, Magali Chemical Communications, Vol. 48, Issue 71 https://doi.org/10.1039/c2cc33921h	journal	January 2012
Benzene-1,3,5-tricarboxamide: a versatile ordering moiety for supramolecular chemistry Cantekin, Seda; de Greef, Tom F. A.; Palmans, Anja R. A. Chemical Society Reviews, Vol. 41, Issue 18 https://doi.org/10.1039/c2cs35156k	journal	January 2012
Tetrabenzoporphyrins: synthetic developments and applications Carvalho, Carla Marisa Brito; Brocksom, Timothy John; de Oliveira, Kleber Thiago Chemical Society Reviews, Vol. 42, Issue 8 https://doi.org/10.1039/c3cs35500d	journal	January 2013
Controlling the growth and shape of chiral supramolecular polymers in water Besenius, P.; Portale, G.; Bomans, P. H. H. Proceedings of the National Academy of Sciences, Vol. 107, Issue 42 https://doi.org/10.1073/pnas.1009592107	journal	October 2010
Solid-phase Pd-catalysed cross-coupling methods for the construction of π-conjugated peptide nanomaterials Sanders, Allix M.; Tovar, John D. Supramolecular Chemistry, Vol. 26, Issue 3-4 https://doi.org/10.1080/10610278.2013.852675	journal	November 2013
Macroscopic Hierarchical Surface Patterning of Porphyrin Trimers via Self-Assembly and Dewetting van Hameren, R.; Schon, P.; van Buul, A. M. Science, Vol. 314, Issue 5804 https://doi.org/10.1126/science.1133004	journal	December 2006
The exciton model in molecular spectroscopy Kasha, M.; Rawls, H. R.; Ashraf El-Bayoumi, M. Pure and Applied Chemistry, Vol. 11, Issue 3-4 https://doi.org/10.1351/pac196511030371	journal	January 1965

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36 MATERIALS SCIENCE
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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electron microscopy
molecular structure
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Title: Solid-Phase Synthesis of Self-Assembling Multivalent π-Conjugated Peptides

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