Hydrogen-bonded donor–acceptor arrays at the solution–graphite interface

Gangamallaiah Velpula, Mengmeng Li, Yunbin Hu, Yulian Zagranyarski, Wojciech Pisula, Klaus Müllen, Kunal S. Mali, Steven De Feyter

Research output: Contribution to journalArticleAcademicpeer-review

5 Citations (Scopus)

Abstract

Controlling the nanoscale morphology of organic thin films represents a critical challenge in the fabrication of organic (opto)electronic devices. The morphology of the (multicomponent) thin films in turn depends on the mutual orientation of the molecular components and their supramolecular packing on the surface. Here, it is shown how the surface co-assembly of electron-donating and -accepting building blocks can be controlled via (supra)molecular design. Hexa-peri-hexabenzocoronene (HBC) derivatives with multiple hydrogen-bonding (H-bonding) sites were synthesized and their co-assembly with alkyl-substituted perylene tetracarboxy diimide (PDI) was studied using scanning tunneling microscopy (STM) at the solution–graphite interface. STM data shows that electron-rich HBCs co-assemble laterally with electron deficient PDIs via preprogrammed H-bonding sites with high fidelity. The surface stoichiometry of the two components could be readily tuned by changing the number of H-bonding sites on the HBC derivatives via organic synthesis. This model study highlights the utility of (supra)molecular design in co-assembly of building blocks relevant for organic electronics.

LanguageEnglish
Pages12071-12077
Number of pages7
JournalChemistry : A European Journal
Volume24
Issue number46
DOIs
StatePublished - 14 Aug 2018

Fingerprint

Graphite
Hydrogen
Hydrogen bonds
Scanning tunneling microscopy
Electrons
Perylene
Derivatives
Thin films
Stoichiometry
Optoelectronic devices
Electronic equipment
Fabrication

Keywords

  • donor–acceptor
  • hydrogen-bonding
  • organic electronics
  • self-assembly
  • STM

Cite this

Velpula, G., Li, M., Hu, Y., Zagranyarski, Y., Pisula, W., Müllen, K., ... De Feyter, S. (2018). Hydrogen-bonded donor–acceptor arrays at the solution–graphite interface. Chemistry : A European Journal, 24(46), 12071-12077. DOI: 10.1002/chem.201803115
Velpula, Gangamallaiah ; Li, Mengmeng ; Hu, Yunbin ; Zagranyarski, Yulian ; Pisula, Wojciech ; Müllen, Klaus ; Mali, Kunal S. ; De Feyter, Steven. / Hydrogen-bonded donor–acceptor arrays at the solution–graphite interface. In: Chemistry : A European Journal. 2018 ; Vol. 24, No. 46. pp. 12071-12077
@article{088ed126cf2a44a0903460013e9fd05b,
title = "Hydrogen-bonded donor–acceptor arrays at the solution–graphite interface",
abstract = "Controlling the nanoscale morphology of organic thin films represents a critical challenge in the fabrication of organic (opto)electronic devices. The morphology of the (multicomponent) thin films in turn depends on the mutual orientation of the molecular components and their supramolecular packing on the surface. Here, it is shown how the surface co-assembly of electron-donating and -accepting building blocks can be controlled via (supra)molecular design. Hexa-peri-hexabenzocoronene (HBC) derivatives with multiple hydrogen-bonding (H-bonding) sites were synthesized and their co-assembly with alkyl-substituted perylene tetracarboxy diimide (PDI) was studied using scanning tunneling microscopy (STM) at the solution–graphite interface. STM data shows that electron-rich HBCs co-assemble laterally with electron deficient PDIs via preprogrammed H-bonding sites with high fidelity. The surface stoichiometry of the two components could be readily tuned by changing the number of H-bonding sites on the HBC derivatives via organic synthesis. This model study highlights the utility of (supra)molecular design in co-assembly of building blocks relevant for organic electronics.",
keywords = "donor–acceptor, hydrogen-bonding, organic electronics, self-assembly, STM",
author = "Gangamallaiah Velpula and Mengmeng Li and Yunbin Hu and Yulian Zagranyarski and Wojciech Pisula and Klaus M{\"u}llen and Mali, {Kunal S.} and {De Feyter}, Steven",
year = "2018",
month = "8",
day = "14",
doi = "10.1002/chem.201803115",
language = "English",
volume = "24",
pages = "12071--12077",
journal = "Chemistry : A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "46",

}

Velpula, G, Li, M, Hu, Y, Zagranyarski, Y, Pisula, W, Müllen, K, Mali, KS & De Feyter, S 2018, 'Hydrogen-bonded donor–acceptor arrays at the solution–graphite interface' Chemistry : A European Journal, vol. 24, no. 46, pp. 12071-12077. DOI: 10.1002/chem.201803115

Hydrogen-bonded donor–acceptor arrays at the solution–graphite interface. / Velpula, Gangamallaiah; Li, Mengmeng; Hu, Yunbin; Zagranyarski, Yulian; Pisula, Wojciech; Müllen, Klaus; Mali, Kunal S.; De Feyter, Steven.

In: Chemistry : A European Journal, Vol. 24, No. 46, 14.08.2018, p. 12071-12077.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Hydrogen-bonded donor–acceptor arrays at the solution–graphite interface

AU - Velpula,Gangamallaiah

AU - Li,Mengmeng

AU - Hu,Yunbin

AU - Zagranyarski,Yulian

AU - Pisula,Wojciech

AU - Müllen,Klaus

AU - Mali,Kunal S.

AU - De Feyter,Steven

PY - 2018/8/14

Y1 - 2018/8/14

N2 - Controlling the nanoscale morphology of organic thin films represents a critical challenge in the fabrication of organic (opto)electronic devices. The morphology of the (multicomponent) thin films in turn depends on the mutual orientation of the molecular components and their supramolecular packing on the surface. Here, it is shown how the surface co-assembly of electron-donating and -accepting building blocks can be controlled via (supra)molecular design. Hexa-peri-hexabenzocoronene (HBC) derivatives with multiple hydrogen-bonding (H-bonding) sites were synthesized and their co-assembly with alkyl-substituted perylene tetracarboxy diimide (PDI) was studied using scanning tunneling microscopy (STM) at the solution–graphite interface. STM data shows that electron-rich HBCs co-assemble laterally with electron deficient PDIs via preprogrammed H-bonding sites with high fidelity. The surface stoichiometry of the two components could be readily tuned by changing the number of H-bonding sites on the HBC derivatives via organic synthesis. This model study highlights the utility of (supra)molecular design in co-assembly of building blocks relevant for organic electronics.

AB - Controlling the nanoscale morphology of organic thin films represents a critical challenge in the fabrication of organic (opto)electronic devices. The morphology of the (multicomponent) thin films in turn depends on the mutual orientation of the molecular components and their supramolecular packing on the surface. Here, it is shown how the surface co-assembly of electron-donating and -accepting building blocks can be controlled via (supra)molecular design. Hexa-peri-hexabenzocoronene (HBC) derivatives with multiple hydrogen-bonding (H-bonding) sites were synthesized and their co-assembly with alkyl-substituted perylene tetracarboxy diimide (PDI) was studied using scanning tunneling microscopy (STM) at the solution–graphite interface. STM data shows that electron-rich HBCs co-assemble laterally with electron deficient PDIs via preprogrammed H-bonding sites with high fidelity. The surface stoichiometry of the two components could be readily tuned by changing the number of H-bonding sites on the HBC derivatives via organic synthesis. This model study highlights the utility of (supra)molecular design in co-assembly of building blocks relevant for organic electronics.

KW - donor–acceptor

KW - hydrogen-bonding

KW - organic electronics

KW - self-assembly

KW - STM

UR - http://www.scopus.com/inward/record.url?scp=85051476082&partnerID=8YFLogxK

U2 - 10.1002/chem.201803115

DO - 10.1002/chem.201803115

M3 - Article

VL - 24

SP - 12071

EP - 12077

JO - Chemistry : A European Journal

T2 - Chemistry : A European Journal

JF - Chemistry : A European Journal

SN - 0947-6539

IS - 46

ER -

Velpula G, Li M, Hu Y, Zagranyarski Y, Pisula W, Müllen K et al. Hydrogen-bonded donor–acceptor arrays at the solution–graphite interface. Chemistry : A European Journal. 2018 Aug 14;24(46):12071-12077. Available from, DOI: 10.1002/chem.201803115