Synthesis, ensemble, and single molecule characterization of a diphenyl-acetylene linked perylenediimide trimer

Tom Vosch, Eduard Fron, Jun Ichi Hotta, Ania Deres, Hiroshi Uji-i, Abdenacer Idrissi, Jaesung Yang, Dongho Kim, Larissa Puhl, Andreas Haeuseler, Klaus Müllen, Frans C. De Schryver, Michel Sliwa, Johan Hofkens

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Perylenediimide (PDI) dyes have attracted a great deal of attention as they possess excellent photochemical stability, high extinction coefficients, and fluorescence quantum yields. The use of multiple PDI chromophores in one synthetic architecture increases their versatile use and functionality even more. However, bringing multiple chromophores in close proximity also leads to interactions among the chromophores and opens up new photophysical pathways. Here, the synthesis and photophysical characterization, both at the ensemble and single molecule level, of a diphenyl-acetylene linked perylenediimide trimer (3PDIAc) is presented. Forster type energy transfer processes like energy hopping and singlet-singlet annihilation among the chromophores are investigated. Despite the lower singlet-singlet annihilation rate of the phenoxy substituted perylenediimide chromophores (356 ps) versus for example perylenemonoimide (10 ps), the system still behaves as a single photon emitter. Sequential fitting of the dipole emission pattern recorded with defocused wide field imaging of single 3PDIAc, immobilized in a PMMA polymer film, demonstrated that emission can switch between sequential emission of all of the chromophores or emission from one chromophore that likely is the lowest in energy.

Original languageEnglish
Pages (from-to)11773-11782
Number of pages10
JournalJournal of Physical Chemistry C
Volume113
Issue number27
DOIs
Publication statusPublished - 2009 Jul 9

Fingerprint

Acetylene
Chromophores
trimers
acetylene
chromophores
Molecules
synthesis
molecules
Light extinction
Quantum yield
Polymethyl Methacrylate
diphenyl
perylenediimide
Polymer films
Energy transfer
proximity
emitters
extinction
Coloring Agents
Photons

All Science Journal Classification (ASJC) codes

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

Cite this

Vosch, T., Fron, E., Hotta, J. I., Deres, A., Uji-i, H., Idrissi, A., ... Hofkens, J. (2009). Synthesis, ensemble, and single molecule characterization of a diphenyl-acetylene linked perylenediimide trimer. Journal of Physical Chemistry C, 113(27), 11773-11782. https://doi.org/10.1021/jp901820y
Vosch, Tom ; Fron, Eduard ; Hotta, Jun Ichi ; Deres, Ania ; Uji-i, Hiroshi ; Idrissi, Abdenacer ; Yang, Jaesung ; Kim, Dongho ; Puhl, Larissa ; Haeuseler, Andreas ; Müllen, Klaus ; De Schryver, Frans C. ; Sliwa, Michel ; Hofkens, Johan. / Synthesis, ensemble, and single molecule characterization of a diphenyl-acetylene linked perylenediimide trimer. In: Journal of Physical Chemistry C. 2009 ; Vol. 113, No. 27. pp. 11773-11782.
@article{6bf504083f0c4217b8e82929cec46a47,
title = "Synthesis, ensemble, and single molecule characterization of a diphenyl-acetylene linked perylenediimide trimer",
abstract = "Perylenediimide (PDI) dyes have attracted a great deal of attention as they possess excellent photochemical stability, high extinction coefficients, and fluorescence quantum yields. The use of multiple PDI chromophores in one synthetic architecture increases their versatile use and functionality even more. However, bringing multiple chromophores in close proximity also leads to interactions among the chromophores and opens up new photophysical pathways. Here, the synthesis and photophysical characterization, both at the ensemble and single molecule level, of a diphenyl-acetylene linked perylenediimide trimer (3PDIAc) is presented. Forster type energy transfer processes like energy hopping and singlet-singlet annihilation among the chromophores are investigated. Despite the lower singlet-singlet annihilation rate of the phenoxy substituted perylenediimide chromophores (356 ps) versus for example perylenemonoimide (10 ps), the system still behaves as a single photon emitter. Sequential fitting of the dipole emission pattern recorded with defocused wide field imaging of single 3PDIAc, immobilized in a PMMA polymer film, demonstrated that emission can switch between sequential emission of all of the chromophores or emission from one chromophore that likely is the lowest in energy.",
author = "Tom Vosch and Eduard Fron and Hotta, {Jun Ichi} and Ania Deres and Hiroshi Uji-i and Abdenacer Idrissi and Jaesung Yang and Dongho Kim and Larissa Puhl and Andreas Haeuseler and Klaus M{\"u}llen and {De Schryver}, {Frans C.} and Michel Sliwa and Johan Hofkens",
year = "2009",
month = "7",
day = "9",
doi = "10.1021/jp901820y",
language = "English",
volume = "113",
pages = "11773--11782",
journal = "Journal of Physical Chemistry C",
issn = "1932-7447",
publisher = "American Chemical Society",
number = "27",

}

Vosch, T, Fron, E, Hotta, JI, Deres, A, Uji-i, H, Idrissi, A, Yang, J, Kim, D, Puhl, L, Haeuseler, A, Müllen, K, De Schryver, FC, Sliwa, M & Hofkens, J 2009, 'Synthesis, ensemble, and single molecule characterization of a diphenyl-acetylene linked perylenediimide trimer', Journal of Physical Chemistry C, vol. 113, no. 27, pp. 11773-11782. https://doi.org/10.1021/jp901820y

Synthesis, ensemble, and single molecule characterization of a diphenyl-acetylene linked perylenediimide trimer. / Vosch, Tom; Fron, Eduard; Hotta, Jun Ichi; Deres, Ania; Uji-i, Hiroshi; Idrissi, Abdenacer; Yang, Jaesung; Kim, Dongho; Puhl, Larissa; Haeuseler, Andreas; Müllen, Klaus; De Schryver, Frans C.; Sliwa, Michel; Hofkens, Johan.

In: Journal of Physical Chemistry C, Vol. 113, No. 27, 09.07.2009, p. 11773-11782.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis, ensemble, and single molecule characterization of a diphenyl-acetylene linked perylenediimide trimer

AU - Vosch, Tom

AU - Fron, Eduard

AU - Hotta, Jun Ichi

AU - Deres, Ania

AU - Uji-i, Hiroshi

AU - Idrissi, Abdenacer

AU - Yang, Jaesung

AU - Kim, Dongho

AU - Puhl, Larissa

AU - Haeuseler, Andreas

AU - Müllen, Klaus

AU - De Schryver, Frans C.

AU - Sliwa, Michel

AU - Hofkens, Johan

PY - 2009/7/9

Y1 - 2009/7/9

N2 - Perylenediimide (PDI) dyes have attracted a great deal of attention as they possess excellent photochemical stability, high extinction coefficients, and fluorescence quantum yields. The use of multiple PDI chromophores in one synthetic architecture increases their versatile use and functionality even more. However, bringing multiple chromophores in close proximity also leads to interactions among the chromophores and opens up new photophysical pathways. Here, the synthesis and photophysical characterization, both at the ensemble and single molecule level, of a diphenyl-acetylene linked perylenediimide trimer (3PDIAc) is presented. Forster type energy transfer processes like energy hopping and singlet-singlet annihilation among the chromophores are investigated. Despite the lower singlet-singlet annihilation rate of the phenoxy substituted perylenediimide chromophores (356 ps) versus for example perylenemonoimide (10 ps), the system still behaves as a single photon emitter. Sequential fitting of the dipole emission pattern recorded with defocused wide field imaging of single 3PDIAc, immobilized in a PMMA polymer film, demonstrated that emission can switch between sequential emission of all of the chromophores or emission from one chromophore that likely is the lowest in energy.

AB - Perylenediimide (PDI) dyes have attracted a great deal of attention as they possess excellent photochemical stability, high extinction coefficients, and fluorescence quantum yields. The use of multiple PDI chromophores in one synthetic architecture increases their versatile use and functionality even more. However, bringing multiple chromophores in close proximity also leads to interactions among the chromophores and opens up new photophysical pathways. Here, the synthesis and photophysical characterization, both at the ensemble and single molecule level, of a diphenyl-acetylene linked perylenediimide trimer (3PDIAc) is presented. Forster type energy transfer processes like energy hopping and singlet-singlet annihilation among the chromophores are investigated. Despite the lower singlet-singlet annihilation rate of the phenoxy substituted perylenediimide chromophores (356 ps) versus for example perylenemonoimide (10 ps), the system still behaves as a single photon emitter. Sequential fitting of the dipole emission pattern recorded with defocused wide field imaging of single 3PDIAc, immobilized in a PMMA polymer film, demonstrated that emission can switch between sequential emission of all of the chromophores or emission from one chromophore that likely is the lowest in energy.

UR - http://www.scopus.com/inward/record.url?scp=67650783949&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=67650783949&partnerID=8YFLogxK

U2 - 10.1021/jp901820y

DO - 10.1021/jp901820y

M3 - Article

VL - 113

SP - 11773

EP - 11782

JO - Journal of Physical Chemistry C

JF - Journal of Physical Chemistry C

SN - 1932-7447

IS - 27

ER -