Effect of Side Chains on Charge Transfer in Quaterthiophene-Naphthalene Diimide Based Donor-Bridge-Acceptor Dyads

Bheemaraju, Amarnath; Pourmand, Mahshid; Yang, Boqian; Surampudi, Sravan K.; Benanti, Travis L.; Achermann, Marc; Barnes, Michael D.; Venkataraman, D.

doi:10.1080/10601325.2011.620473

Cited by 9 publications

(5 citation statements)

References 19 publications

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“…For the electron-donor unit, we chose quaterthiophene (OT4) because the synthesis of peptides embedded with this π-conjugated moiety has already been optimized. , Electron accepting naphthalene diimide (NDI) was selected for the acceptor, due to the option of facile incorporation via lysine side-chains. Venkataraman and co-workers have previously used this donor–acceptor pair in organic media and found it to be an ideal system for electron transfer due to the lack of spectral overlap between the emission wavelengths of OT4 and absorption wavelengths of NDI (to discourage nonpolar energy transfer) and beneficial LUMO level positioning (to encourage transfer of excited electrons) . We prepared a series of electron donor–acceptor pairs with varied separating peptide lengths alongside the analogous control molecules bearing the OT4 donor element only.…”

Section: Resultsmentioning

confidence: 99%

Photoinduced Electron Transfer within Supramolecular Donor–Acceptor Peptide Nanostructures under Aqueous Conditions

et al. 2016

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We report the synthesis, self-assembly, and electron transfer capabilities of peptide-based electron donor-acceptor molecules and supramolecular nanostructures. These modified peptides contain π-conjugated oligothiophene electron donor cores that are peripherally substituted with naphthalene diimide electron acceptors installed via imidation of site-specific lysine residues. These molecules self-assemble into one-dimensional nanostructures in aqueous media, as shown through steady-state absorption, photoluminescence, and circular dichroism spectra, as well as transmission electron microscopy. Excitation of the oligothiophene donor moieties results in electron transfer to the acceptor units, ultimately creating polar, charge-separated states that persist for over a nanosecond as observed with transient absorption spectroscopy. This study demonstrates how transient electric fields can be engineered into aqueous nanomaterials of biomedical relevance through external, temporally controlled photonic inputs.

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Section: Resultsmentioning

confidence: 99%

Photoinduced Electron Transfer within Supramolecular Donor–Acceptor Peptide Nanostructures under Aqueous Conditions

et al. 2016

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“…The first of which being a π‐π* transition band as observed in the thin film absorption spectra centered at 368, 391, and 412 nm for PNDI‐2fTh, PNDI‐3fTh, and PNDI‐4fTh, respectively. The second distinct absorption peak in the spectra can be attributed to a strong intramolecular charge transfer (ICT) at longer wavelengths . Furthermore, the ICT peak showed a progressive red‐shift from 560 nm ( PNDI‐2fTh ), to 700 nm ( PNDI‐3fTh ), to 710 nm ( PNDI‐4fTh ) in the solid state.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of fused-thiophene containing naphthalene diimide n -type copolymers for organic thin film transistor and all-polymer solar cell applications

Yuan

Durban

Kazarinoff

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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Naphthalene diimide copolymers are attractive ntype materials due to their high electron affinities, high electron mobilities, and exceptional stability. Herein, we report a series of NDI-fused-thiophene based copolymers with each copolymer differing in the number of fused thiophenes in the donor monomer. Increasing the number of fused-thiophene moieties within an NDI-copolymer backbone is shown to not only enable tuning of the electronic structure but also improve charge mobilities within the active layer of organic field-effect transistors. Electron mobilities and on/off ratios as high as 0.012 cm 2 V 21 s -1 and I on / I off > 10 5 were measured from n-channel thin-film transistors fabricated using NDI-xfTh copolymers. Bulk heterojunction solar cell devices were also fabricated from the NDI-xfTh copolymer series in blends with poly(3-hexylthiophene) (P3HT) with PNDI-4fTh-based devices yielding the largest J sc (0.57 mA cm 22 ) and fill factor (55%) in addition to the highest measured PCE for this series (0.13%).

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“…While Müllen and co-workers primarily focus on dyads composed of hexa-peri-hexabenzocoronene (HBC) linked to perylenetetracarboxy-diimide (PDI) and -monoimide (PMI), ,,− Aidi and co-workers have developed amphiphilic oligothiophene-C 60 and HBC-C 60 dyads . Venkataraman and co-workers have studied amphiphilic naphthalimide (NI)-naphthyl and naphthalene diimide (NDI)-quaterthiophene (QT) D–A dyads, while Würthner et al studied the effects of hydrogen bonding on the assembly of oligo(p-phenylene vinylenes) (OPVs) and perylene bisimides (PERYs) into p–n heterojunctions …”

Section: Introductionmentioning

confidence: 99%

Time-Dependent Solid-State Polymorphism of a Series of Donor–Acceptor Dyads

Peebles

Alvey

Lynch

et al. 2013

Crystal Growth & Design

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In order to exploit the use of favorable electrostatic interactions between aromatic units in directing the assembly of donor-acceptor (D-A) dyads, the present work examines the ability of conjugated aromatic D-A dyads with symmetric side chains to exhibit solid-state polymorphism as a function of time during the solid formation process. Four such dyads were synthesized and their packing in the solid-state from either slower (10-20 days) or faster (1-2 days) evaporation from solvent was investigated using single crystal X-ray analysis and powder X-ray diffraction. Two of the dyads exhibited tail-to-tail (A-A) packing upon slower evaporation from solvent and head-to-tail (D-A) packing upon faster evaporation from solvent. A combination of single crystal analysis and XRD patterns were used to create models wherein a packing model for the other two dyads is proposed. Our findings suggest that while side chain interactions in asymmetric aromatic dyads can play an important role in enforcing segregated D-A dyad assembly, slowly evaporating symmetrically substituted aromatic dyads allows for favorable electrostatic interactions between the aromatic moieties to facilitate the organization of the dyads in the solid-state.

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Effect of Side Chains on Charge Transfer in Quaterthiophene-Naphthalene Diimide Based Donor-Bridge-Acceptor Dyads

Cited by 9 publications

References 19 publications

Photoinduced Electron Transfer within Supramolecular Donor–Acceptor Peptide Nanostructures under Aqueous Conditions

Photoinduced Electron Transfer within Supramolecular Donor–Acceptor Peptide Nanostructures under Aqueous Conditions

Synthesis and characterization of fused-thiophene containing naphthalene diimide n -type copolymers for organic thin film transistor and all-polymer solar cell applications

Time-Dependent Solid-State Polymorphism of a Series of Donor–Acceptor Dyads

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