Chloride-promoted self-assembly and photoluminescence of naphthalene diimides tethered to polyacetylene

With the aim of developing a system with tunable self-assembly of π-conjugated building blocks, an optically active helical polyacetylene bearing amide groups and naphthalene diimide (NDI) derivatives in the side chains is reported. The helical conformation of the polymer backbone and the stacking pattern of the pendant NDIs can be regulated by adding trifluoroacetic acid or specific solvents or anions. In particular, Cl− can induce a dynamic reorganization in molecular arrangement of naphthalenediimides from H-type to J-type aggregates along with turning fluorescence emission on at 515 nm. Consequently, the self-assembly of NDIs is effectively controlled, which can lead to the regulation of the properties of NDI-based materials. To the best of our knowledge, this is the first time that the optically active helical polyacetylene has been applied in the regulation of stacking modes of NDIs. This strategy has shown great potential for anion recognition and the design of stimulus-responsive materials.

[1]  Lichun Dong,et al.  Naphthalene diimide based near-infrared luminogens with aggregation-induced emission characteristics for biological imaging and high mobility ambipolar transistors , 2020, Science China Chemistry.

[2]  S. Richter,et al.  Selective targeting of mutually exclusive DNA G-quadruplexes: HIV-1 LTR as paradigmatic model , 2020, Nucleic acids research.

[3]  S. Jenekhe,et al.  Effects of a Fluorinated Donor Polymer on the Morphology, Photophysics, and Performance of All-Polymer Solar Cells based on Naphthalene Diimide-Arylene Copolymer Acceptors. , 2020, ACS applied materials & interfaces.

[4]  R. Bhosale,et al.  Aggregation-induced emission characteristics and solvent triggered hierarchical self-assembled chiral superstructures of naphthalenediimide amphiphiles , 2020 .

[5]  Mingyan Wu,et al.  Atropisomer-based construction of macrocyclic hosts that selectively recognize tryptophan from standard amino acids. , 2019, Chemical Communications.

[6]  F. Wang,et al.  Thermoresponsive Dendronized Poly(phenylacetylene)s Showing Tunable Helicity , 2019, Macromolecules.

[7]  Thimmaiah Govindaraju,et al.  Amino Acids and Peptides as Functional Components in Arylenediimide-Based Molecular Architectonics , 2019 .

[8]  T. Bell,et al.  Harnessing Brightness in Naphthalene Diimides. , 2019, Chemistry.

[9]  A. Zanelli,et al.  Thermodynamically versus Kinetically Controlled Self-Assembly of a Naphthalenediimide-Thiophene Derivative: From Crystalline, Fluorescent, n-Type Semiconducting 1D Needles to Nanofibers. , 2019, ACS applied materials & interfaces.

[10]  Jie Zhang,et al.  Synthesis and thermo-responsive behavior of helical polyacetylenes derived from proline. , 2018, Chemical communications.

[11]  S. Saha.  Anion-Induced Electron Transfer. , 2018, Accounts of chemical research.

[12]  S. Jenekhe,et al.  All-Polymer Solar Cells with 9.4% Efficiency from Naphthalene Diimide-Biselenophene Copolymer Acceptor , 2018, Chemistry of Materials.

[13]  Mei-Jin Lin,et al.  Structural insights into the aggregation-induced emission mechanism of naphthalene diimide solids , 2017 .

[14]  M. Calderón,et al.  Unexpected Chiro-Thermoresponsive Behavior of Helical Poly(phenylacetylene)s Bearing Elastin-Based Side Chains. , 2017, Angewandte Chemie.

[15]  Rizhe Jin,et al.  An Optically Active Polymer for Broad-Spectrum Enantiomeric Recognition of Chiral Acids. , 2017, Chemistry.

[16]  Zongxia Guo,et al.  Helical Conformations of Poly(3,5-disubstituted phenylacetylene)s Tuned by Pendant Structure and Solvent , 2017 .

[17]  J. M. Pérez-Victoria,et al.  Synthesis, Binding Properties, and Differences in Cell Uptake of G-Quadruplex Ligands Based on Carbohydrate Naphthalene Diimide Conjugates. , 2017, Chemistry.

[18]  T. Satoh,et al.  Polyacetylenes as Colorimetric and Fluorescent Chemosensor for Anions , 2017 .

[19]  A. Zhang,et al.  Stimuli-Responsive Polyacetylenes and Dendronized Poly(phenylacetylene)s , 2017 .

[20]  Zhiyuan Zhao,et al.  Reversible Cis-Cisoid to Cis-Transoid Helical Structure Transition in Poly(3,5-disubstituted phenylacetylene)s , 2016 .

[21]  R. Riguera,et al.  Supramolecular Assemblies from Poly(phenylacetylene)s. , 2016, Chemical reviews.

[22]  Xuan Sun,et al.  H-Bonding and charging mediated aggregation and emission for fluorescence turn-on detection of hydrazine hydrate. , 2015, Chemical communications.

[23]  E. Prasad,et al.  Orange red emitting naphthalene diimide derivative containing dendritic wedges: aggregation induced emission (AIE) and detection of picric acid (PA) , 2015 .

[24]  T. Govindaraju,et al.  Crystallographic insight-guided nanoarchitectonics and conductivity modulation of an n-type organic semiconductor through peptide conjugation. , 2015, Chemical communications.

[25]  Zhiyuan Hu,et al.  A fluorescent Arg-Gly-Asp (RGD) peptide-naphthalenediimide (NDI) conjugate for imaging integrin α(v)β(3) in vitro. , 2015, Chemical communications.

[26]  S. Seki,et al.  Semiconducting Nanotubes by Intrachain Folding Following Macroscopic Assembly of a Naphthalene–Diimide (NDI) Appended Polyurethane , 2015 .

[27]  Sijbren Otto,et al.  Supramolecular systems chemistry. , 2015, Nature nanotechnology.

[28]  Guichao Kuang,et al.  Thermoresponsive Helical Poly(phenylacetylene)s , 2014 .

[29]  Subi J. George,et al.  Carbonate linkage bearing naphthalenediimides: self-assembly and photophysical properties. , 2014, Chemistry.

[30]  J. Seco,et al.  Controlled modulation of the helical sense and the elongation of poly(phenylacetylene)s by polar and donor effects , 2013 .

[31]  S. George,et al.  Synthesis and self-assembly of a C3-symmetric benzene-1,3,5-tricarboxamide (BTA) anchored naphthalene diimide disc , 2013 .

[32]  S. Saha,et al.  Boundaries of anion/naphthalenediimide interactions: from anion-π interactions to anion-induced charge-transfer and electron-transfer phenomena. , 2012, Journal of the American Chemical Society.

[33]  S. Saha,et al.  Electronically regulated thermally and light-gated electron transfer from anions to naphthalenediimides. , 2011, Journal of the American Chemical Society.

[34]  S. George,et al.  Green fluorescent organic nanoparticles by self-assembly induced enhanced emission of a naphthalene diimide bolaamphiphile. , 2011, Nanoscale.

[35]  M. R. Molla,et al.  Structural Variations on Self-Assembly and Macroscopic Properties of 1,4,5,8-Naphthalene-diimide Chromophores , 2011 .

[36]  S. Saha,et al.  Fluoride ion sensing by an anion-π interaction. , 2010, Journal of the American Chemical Society.

[37]  C. Jaroniec,et al.  Amphiphilic self-assembly of an n-type nanotube. , 2010, Angewandte Chemie.

[38]  J. Parquette,et al.  A pi-conjugated hydrogel based on an Fmoc-dipeptide naphthalene diimide semiconductor. , 2010, Chemical communications.

[39]  J. Parquette,et al.  Self-assembly of 1-D n-type nanostructures based on naphthalene diimide-appended dipeptides. , 2009, Journal of the American Chemical Society.

[40]  S. Langford,et al.  Chemistry of naphthalene diimides. , 2008, Chemical Society reviews.

[41]  Y. Inai,et al.  Synthesis of helical poly(N-propargylamides) carrying azobenzene moieties in side chains. Reversible arrangement-disarrangement of helical side chain arrays upon photoirradiation keeping helical main chain intact , 2007 .

[42]  Yongqiang Dong,et al.  Synthesis, helicity, and chromism of optically active poly(phenylacetylene)s carrying different amino acid moieties and pendant terminal groups. , 2006, The journal of physical chemistry. B.

[43]  J. Tabei,et al.  Chiroptical study and conformation analysis of helical polymers surrounded by helical hydrogen-bonding strands , 2006 .

[44]  J. Tabei,et al.  Stereoregular poly(N-propargylcarbamates) having helical conformation stabilized by the intramolecular hydrogen bonds , 2003 .