A porphyrin-based molecular tweezer: Guest-induced switching of forward and backward photoinduced energy transfer

Hongsik Yoon, Jong Min Lim, Hyuk Chan Gee, Chi Hwa Lee, Young Hwan Jeong, Dongho Kim, Woo Dong Jang

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

A bisindole-bridged-porphyrin tweezer (1), a pair of zinc porphyrins (P Zn 's) connected to bisindole bridge (BB) via the Cu I -mediated alkyne-azide click chemistry, exhibited unique switching in forward and backward photoinduced energy transfer by specific guest bindings. The addition of Cu 2+ caused a change in electronic absorption and fluorescence quenching of 1. MALDI-TOF-MS and FT-IR analyses indicated the formation of stable coordination complex between 1 and Cu 2+ (1-Cu(II)). Without Cu 2+ coordination, the excitation energy flows from BB to P Zn 's with significantly high energy transfer efficiency. In contrast, the direction of energy flow in 1 was completely reversed by the coordination of Cu 2+ . The difference in fluorescence quantum yield between 1 and 1-Cu(II) indicates that more than 95% of excitation energy of P Zn flows into Cu(II)-coordinated BB. The energy transfer efficiency was further controlled by bidentate ligand coordination onto 1-Cu(II). When pyrophosphate ion was added to 1-Cu(II), the recovery of fluorescence emission from P Zn was observed. The quantum mechanical calculations indicated that the Cu(II)-coordinated BB has square planar geometry, which can be distorted to form octahedral geometry due to the coordination of bidentate ligands.

Original languageEnglish
Pages (from-to)1672-1679
Number of pages8
JournalJournal of the American Chemical Society
Volume136
Issue number4
DOIs
Publication statusPublished - 2014 Jan 29

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Energy Transfer
Porphyrins
Energy transfer
Fluorescence
Excitation energy
Click Chemistry
Ligands
Zinc
Alkynes
Azides
Matrix-Assisted Laser Desorption-Ionization Mass Spectrometry
Coordination Complexes
Geometry
Quantum yield
Ions
Quenching
Recovery
zinc hematoporphyrin

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Yoon, Hongsik ; Lim, Jong Min ; Gee, Hyuk Chan ; Lee, Chi Hwa ; Jeong, Young Hwan ; Kim, Dongho ; Jang, Woo Dong. / A porphyrin-based molecular tweezer : Guest-induced switching of forward and backward photoinduced energy transfer. In: Journal of the American Chemical Society. 2014 ; Vol. 136, No. 4. pp. 1672-1679.
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abstract = "A bisindole-bridged-porphyrin tweezer (1), a pair of zinc porphyrins (P Zn 's) connected to bisindole bridge (BB) via the Cu I -mediated alkyne-azide click chemistry, exhibited unique switching in forward and backward photoinduced energy transfer by specific guest bindings. The addition of Cu 2+ caused a change in electronic absorption and fluorescence quenching of 1. MALDI-TOF-MS and FT-IR analyses indicated the formation of stable coordination complex between 1 and Cu 2+ (1-Cu(II)). Without Cu 2+ coordination, the excitation energy flows from BB to P Zn 's with significantly high energy transfer efficiency. In contrast, the direction of energy flow in 1 was completely reversed by the coordination of Cu 2+ . The difference in fluorescence quantum yield between 1 and 1-Cu(II) indicates that more than 95{\%} of excitation energy of P Zn flows into Cu(II)-coordinated BB. The energy transfer efficiency was further controlled by bidentate ligand coordination onto 1-Cu(II). When pyrophosphate ion was added to 1-Cu(II), the recovery of fluorescence emission from P Zn was observed. The quantum mechanical calculations indicated that the Cu(II)-coordinated BB has square planar geometry, which can be distorted to form octahedral geometry due to the coordination of bidentate ligands.",
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A porphyrin-based molecular tweezer : Guest-induced switching of forward and backward photoinduced energy transfer. / Yoon, Hongsik; Lim, Jong Min; Gee, Hyuk Chan; Lee, Chi Hwa; Jeong, Young Hwan; Kim, Dongho; Jang, Woo Dong.

In: Journal of the American Chemical Society, Vol. 136, No. 4, 29.01.2014, p. 1672-1679.

Research output: Contribution to journalArticle

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T2 - Guest-induced switching of forward and backward photoinduced energy transfer

AU - Yoon, Hongsik

AU - Lim, Jong Min

AU - Gee, Hyuk Chan

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AU - Jeong, Young Hwan

AU - Kim, Dongho

AU - Jang, Woo Dong

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