Adjusting aggregation modes and photophysical and photovoltaic properties of diketopyrrolopyrrole-based small molecules by introducing B←N bonds

Shuting Pang, Miriam Más-Montoya, Manjun Xiao, Chunhui Duan (Corresponding author), Zhenfeng Wang, Xi Liu, René A.J. Janssen, Gang Yu, Fei Huang (Corresponding author), Yong Cao

Research output: Contribution to journalArticleAcademicpeer-review

1 Citation (Scopus)

Abstract

The packing mode of small-molecular semiconductors in thin films is an important factor that controls the performance of their optoelectronic devices. Designing and changing the packing mode by molecular engineering is challenging. Three structurally related diketopyrrolopyrrole (DPP)-based compounds were synthesized to study the effect of replacing C−C bonds by isoelectronic dipolar B←N bonds. By replacing one of the bridging C−C bonds on the peripheral fluorene units of the DPP molecules by a coordinative B←N bond and changing the B←N bond orientation, the optical absorption, fluorescence, and excited-state lifetime of the compounds can be tuned. The substitution alters the preferential aggregation of the molecules in the solid state from H-type (for C−C) to J-type (for B←N). Introducing B←N bonds thus provides a subtle way of controlling the packing mode. The photovoltaic properties of the compounds were evaluated in bulk heterojunctions with a fullerene acceptor and showed moderate performance as a consequence of suboptimal morphologies, bimolecular recombination, and triplet-state formation.

LanguageEnglish
Pages564-572
Number of pages9
JournalChemistry - A European Journal
Volume25
Issue number2
DOIs
StatePublished - 7 Jan 2019

Fingerprint

Agglomeration
Molecules
Fullerenes
Excited states
Crystal orientation
Optoelectronic devices
Light absorption
Heterojunctions
Substitution reactions
Fluorescence
Semiconductor materials
Thin films
fluorene

Keywords

  • aggregation
  • B−N bonds
  • photovoltaic properties
  • semiconductors
  • thin films

Cite this

Pang, Shuting ; Más-Montoya, Miriam ; Xiao, Manjun ; Duan, Chunhui ; Wang, Zhenfeng ; Liu, Xi ; Janssen, René A.J. ; Yu, Gang ; Huang, Fei ; Cao, Yong. / Adjusting aggregation modes and photophysical and photovoltaic properties of diketopyrrolopyrrole-based small molecules by introducing B←N bonds. In: Chemistry - A European Journal. 2019 ; Vol. 25, No. 2. pp. 564-572
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Adjusting aggregation modes and photophysical and photovoltaic properties of diketopyrrolopyrrole-based small molecules by introducing B←N bonds. / Pang, Shuting; Más-Montoya, Miriam; Xiao, Manjun; Duan, Chunhui (Corresponding author); Wang, Zhenfeng; Liu, Xi; Janssen, René A.J.; Yu, Gang; Huang, Fei (Corresponding author); Cao, Yong.

In: Chemistry - A European Journal, Vol. 25, No. 2, 07.01.2019, p. 564-572.

Research output: Contribution to journalArticleAcademicpeer-review

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