Highly Ordered Assembly of π-Stacked Distyrylbenzenes by Oligoadenines

Abstract

A well-defined nanofibrous structure with lengths of several hundred nanometers and cross-sectional width of a single size (∼6 ± 0.5 nm) was self-assembled by oligoadenines, dA(20), and thymine-appended distyrylbenzene through binary complementary A-T hydrogen bond formation and the strong π-π stacking interactions. This demonstrated a useful supramolecular self-assembling approach to control the packing order of π-conjugated molecules and provided a practical means to enhance the optical properties of a material.

Energy Transfer in Single-Stranded DNA-Templated Stacks of Naphthalene Chromophores

“…Chromophores that harness the specific bonding mechanisms to DNA can then be designed, such as multivalent guests that bond to DNA with high efficiencies . This results in the synthesis of samples with specific packing orders that enhance the electronic and optical properties of a material …”

“…21 This results in the synthesis of samples with specific packing orders that enhance the electronic and optical properties of a material. 22 DNA-templated systems have been used in a multitude of ways, for example, as force sensors, 23 molecular beacons, 24 and molecular wires. 25,26 All of these applications rely on resonance energy transfer (RET) between luminescent dye molecules, and much effort has thus been devoted to understanding and improving such processes.…”

Phenylenevinylene conjugated oligoelectrolytes as fluorescent dyes for mammalian cell imaging

“…Each COE has been prepared according to a literature precedent. 23,25 Previous reports describing the interaction of ionic and polar group-functionalized distyrylbenzenes with double 26 or single 27 stranded DNA motivated us to ascertain if cell nuclei staining could be achieved using DSBN + , DSSN + , and COE1-5C.…”

Reinforced Self-Assembly of Donor–Acceptor π-Conjugated Molecules to DNA Templates by Dipole–Dipole Interactions Together with Complementary Hydrogen Bonding Interactions for Biomimetics

“…Herein, we describe a design and synthesis of thymine-substituted donor–acceptor π-conjugated molecules DSB-DAT and an investigation of the supramolecular assembly of laterally DSB-DAT and complementary oligoadenines templates, dA 20 and dA 40 , through adenine-thymine (A-T) hydrogen-bonding and dipole–dipole interactions, giving rise to a stability-enhanced nanofibrous assembly. Specifically, our results have demonstrated for the first time that the dipole–dipole interactions among the polar molecules are stronger and useful to reinforce the assembly of donor–acceptor π-conjugated molecules to DNA templates and the formation of the stable and robust supramolecular nanofibrous complexes together with the complementary hydrogen bonding interactions, as compared with nonpolar molecules . The ability to self-assemble or organize this class of dipolar molecules by means of specific sequence of DNA template strand could also contribute to the further development of the nanophotonics, and the nano-optoelectronics as donor–acceptor type structure motif is highly active and useful for multiphoton absorption, photovoltaic effect, , charge transfer, , and light emission .…”

“…The ability to self-assemble or organize this class of dipolar molecules by means of specific sequence of DNA template strand could also contribute to the further development of the nanophotonics, and the nano-optoelectronics as donor–acceptor type structure motif is highly active and useful for multiphoton absorption, photovoltaic effect, , charge transfer, , and light emission . Some examples of the use of the ssDNA as a template to assemble π-conjugated molecules into well-defined aggregates or nanostructures to achieve desirable and interesting functional properties have been exemplified. ,− …”