Peptide-Driven Charge-Transfer Organogels Built from Synergetic Hydrogen Bonding and Pyrene-Naphthalenediimide Donor-Acceptor Interactions

被引：27

作者：

Bartocci, Silvia ^{[1
]}

Berrocal, Jose Augusto ^{[2
]}

Guarracino, Paola ^{[1
]}

Grillaud, Maxime ^{[2
]}

Franco, Lorenzo ^{[1
]}

Mba, Miriam ^{[1
]}

机构：

[1] Univ Padua, Dept Chem Sci, Via Marzolo 1, I-35131 Padua, Italy

[2] Eindhoven Univ Technol, Inst Complex Mol Syst, POB 513, NL-5600 MB Eindhoven, Netherlands

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 12期

关键词：

charge transfer; EPR spectroscopy; gels; peptides; self-assembly; TRANSFER NANOSTRUCTURES; SUPRAMOLECULAR CHIRALITY; ORGANIC SEMICONDUCTORS; NANOFIBROUS HYDROGELS; TUNABLE MORPHOLOGY; TRANSFER COMPLEXES; SELF; SOLVENT; DIIMIDES; AMPHIPHILES;

D O I：

10.1002/chem.201704487

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The peptide-driven formation of charge transfer (CT) supramolecular gels featuring both directional hydrogen-bonding and donor-acceptor (D-A) complexation is reported. Our design consists of the coassembly of two dipeptide-chromophore conjugates, namely diphenylalanine (FF) dipeptide conveniently functionalized at the N-terminus with either a pyrene (Py-1, donor) or naphthalene diimide (NDI-1, acceptor). UV/Vis spectroscopy confirmed the formation of CT complexes. FTIR and H-1 NMR spectroscopy studies underlined the pivotal role of hydrogen bonding in the gelation process, and electronic paramagnetic resonance (EPR) measurements unraveled the advantage of preorganized CT supramolecular architectures for charge transport over solutions containing non-coassembled D and A molecular systems.

引用

页码：2920 / 2928

页数：9

共 74 条

[1] Functional Supramolecular Polymers [J].

Aida, T. ;

Meijer, E. W. ;

Stupp, S. I. .

SCIENCE, 2012, 335 (6070) :813-817

[2] Functional Naphthalene Diimides: Synthesis, Properties, and Applications [J].

Al Kobaisi, Mohammad ;

Bhosale, Sidhanath V. ;

Latham, Kay ;

Raynor, Aaron M. ;

Bhosale, Sheshanath V. .

CHEMICAL REVIEWS, 2016, 116 (19) :11685-11796

[3] Spectroscopy of naphthalene diimides and their anion radicals [J].

Andric, G ;

Boas, JF ;

Bond, AM ;

Fallon, GD ;

Ghiggino, KP ;

Hogan, CF ;

Hutchison, JA ;

Lee, MAP ;

Langford, SJ ;

Pilbrow, JR ;

Troup, GJ ;

Woodward, CP .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2004, 57 (10) :1011-1019

[4]

[Anonymous], 2014, ANGEW CHE

[5] Kinetically Controlled Coassembly of Multichromophoric Peptide Hydrogelators and the Impacts on Energy Transport [J].

Ardona, Herdeline Ann M. ;

Draper, Emily R. ;

Citossi, Francesca ;

Wallace, Matthew ;

Serpell, Louise C. ;

Adams, Dave J. ;

Tovar, John D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (25) :8685-8692

[6] Sequence-dependent mechanical, photophysical and electrical properties of pi-conjugated peptide hydrogelators [J].

Ardona, Herdeline Ann M. ;

Besar, Kalpana ;

Togninalli, Matteo ;

Katz, Howard E. ;

Tovar, John D. .

JOURNAL OF MATERIALS CHEMISTRY C, 2015, 3 (25) :6505-6514

[7] Charge-Transfer-Assisted Supramolecular 1D Nanofibers through a Cholesteric Structure-Directing Agent: Self-Assembly Design for Supramolecular Optoelectronic Materials [J].

Babu, Thunga Madhu ;

Prasad, Edamana .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (34) :11972-11975

[8] Differential Self-Assembly and Tunable Emission of Aromatic Peptide Bola-Amphiphiles Containing Perylene Bisimide in Polar Solvents Including Water [J].

Bai, Shuo ;

Debnath, Sisir ;

Javid, Nadeem ;

Frederix, Pim W. J. M. ;

Fleming, Scott ;

Pappas, Charalampos ;

Ulijn, Rein V. .

LANGMUIR, 2014, 30 (25) :7576-7584

[9] Solvent-tunable morphology and emission of pyrene-dipeptide organogels [J].

Bartocci, S. ;

Morbioli, I. ;

Maggini, M. ;

Mba, M. .

JOURNAL OF PEPTIDE SCIENCE, 2015, 21 (12) :871-878

[10] Charge- Transfer Complex Formation in Gelation: The Role of Solvent Molecules with Different Electron- Donating Capacities [J].

Basak, Shibaji ;

Bhattacharya, Sumantra ;

Datta, Ayan ;

Banerjee, Arindam .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (19) :5721-5726

← 1 2 3 4 5 6 7 8 →