Superstructures of diketopyrrolopyrrole donors and perylenediimide acceptors formed by hydrogen-bonding and π···π stacking

Stephen Rieth, Zhong Li, Charlotte E. Hinkle, Carmen X. Guzman, Jungeun J. Lee, Samer I. Nehme, Adam Braunschweig

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Synthetic supramolecular systems can provide insight into how complex biological systems organize as well as produce self-organized systems with functionality comparable to their biological counterparts. Herein, we study the assembly into superstructures of a system composed of diketopyrrolopyrrole (DPP) donors with chiral and achiral side chains that can form triple hydrogen bonds with perylene diimide (PDI) acceptors into superstructures. The homoaggregation of the individual components as well as the heteroaggregate formation, as a result of π···π stacking and H-bonding, were studied by variable-temperature UV/vis and CD spectroscopies and electronic structure theory calculations. It was found that, upon cooling, the achiral PDIs bind to disordered DPP stacks, which drives the formation of chiral superstructures. A new thermodynamic model was developed for this unprecedented assembly that is able to isolate the thermodynamic binding parameters (ΔH, ΔS) for all the different noncovalent contacts that drive the assembly. This novel assembly as well as the quantitative model described in this work may help researchers develop complex self-assembled systems with emergent properties that arise as a direct result of their supramolecular structures.

Original languageEnglish (US)
Pages (from-to)11347-11356
Number of pages10
JournalJournal of Physical Chemistry C
Volume117
Issue number21
DOIs
StatePublished - May 30 2013

Fingerprint

Hydrogen bonds
assembly
hydrogen
Perylene
Thermodynamics
thermodynamics
Biological systems
Electronic structure
Spectroscopy
hydrogen bonds
electronic structure
Cooling
cooling
perylenediimide
spectroscopy
Temperature
temperature

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Electronic, Optical and Magnetic Materials
  • Surfaces, Coatings and Films
  • Energy(all)

Cite this

Rieth, S., Li, Z., Hinkle, C. E., Guzman, C. X., Lee, J. J., Nehme, S. I., & Braunschweig, A. (2013). Superstructures of diketopyrrolopyrrole donors and perylenediimide acceptors formed by hydrogen-bonding and π···π stacking. Journal of Physical Chemistry C, 117(21), 11347-11356. https://doi.org/10.1021/jp400918z

Superstructures of diketopyrrolopyrrole donors and perylenediimide acceptors formed by hydrogen-bonding and π···π stacking. / Rieth, Stephen; Li, Zhong; Hinkle, Charlotte E.; Guzman, Carmen X.; Lee, Jungeun J.; Nehme, Samer I.; Braunschweig, Adam.

In: Journal of Physical Chemistry C, Vol. 117, No. 21, 30.05.2013, p. 11347-11356.

Research output: Contribution to journalArticle

Rieth, Stephen ; Li, Zhong ; Hinkle, Charlotte E. ; Guzman, Carmen X. ; Lee, Jungeun J. ; Nehme, Samer I. ; Braunschweig, Adam. / Superstructures of diketopyrrolopyrrole donors and perylenediimide acceptors formed by hydrogen-bonding and π···π stacking. In: Journal of Physical Chemistry C. 2013 ; Vol. 117, No. 21. pp. 11347-11356.
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