Borafluorenes and polyborafluorenes boron doped varients of fluorene
type: CreativeWork
description: A series of novel boron containing variants of fluorene were synthesized. Boron was incorporated synthetically via lithium halogen exchange and Grignard reaction pathways. Once incorporated, the borafluorene could be polymerized or undergo further functionalization via Yamamoto and Stille coupling reactions. This incorporation of boron into a conjugated system imparted Lewis acidic and electron deficient properties into a conjugated system. It is our hope that this will dope fluorene and create novel n-type semiconductors. A novel polymer of borafluorene, poly(9-borafluorene) (P9BF) was synthesized. HOMO and LUMO levels of P9BF were estimated by cyclic voltammetry. As predicted in prior DFT studies, P9BF has a reduced band gap and a lower lying LUMO compared with polyfluorene. To examine how the HOMO and LUMO levels of borafluorene systems could be tuned, copolymers of 9-borafluorene were synthesized. Four of the copolymers were a series of donor-acceptor (DA) type copolymers. A borafluorene-fluorene (P9BF-OF) copolymer and borafluorene-diketopyrrolopyrrole (P9BF-DPP), as an acceptor-acceptor (AA) copolymer were also synthesized. The series of DA copolymers showed higher energy HOMO and LUMO levels in correlation with the relative donating ability of the donor monomer. P9BF-OF has a reduced LUMO level in comparison with P9BF. P9BF-DPP has a very low band gap (1.8eV), with absorption well into the near-IR region. To examine ways to make borafluorene more air stable, a series of borafluorenes bearing bismethylmethoxyphenyl (BMMP) ligands were investigated. Interestingly, ii bismethylmethoxyphenyl-borafluorene (BMMP-BF) exhibits an exceptionally large Stokes shift of 16000 cm-1. To extend the conjugation and change the Stokes shift, thiophene containing derivatives BMMP-BF-T, BMMP-BF-2T, and BMMP-BF-3T were synthesized. These thiophene containing compounds exhibited anomalous two wavelength fluorescence. During our fluoride titration experiments, we noticed spectral im…
abstract: A series of novel boron containing variants of fluorene were synthesized. Boron was incorporated synthetically via lithium halogen exchange and Grignard reaction pathways. Once incorporated, the borafluorene could be polymerized or undergo further functionalization via Yamamoto and Stille coupling reactions. This incorporation of boron into a conjugated system imparted Lewis acidic and electron deficient properties into a conjugated system. It is our hope that this will dope fluorene and create novel n-type semiconductors. A novel polymer of borafluorene, poly(9-borafluorene) (P9BF) was synthesized. HOMO and LUMO levels of P9BF were estimated by cyclic voltammetry. As predicted in prior DFT studies, P9BF has a reduced band gap and a lower lying LUMO compared with polyfluorene. To examine how the HOMO and LUMO levels of borafluorene systems could be tuned, copolymers of 9-borafluorene were synthesized. Four of the copolymers were a series of donor-acceptor (DA) type copolymers. A borafluorene-fluorene (P9BF-OF) copolymer and borafluorene-diketopyrrolopyrrole (P9BF-DPP), as an acceptor-acceptor (AA) copolymer were also synthesized. The series of DA copolymers showed higher energy HOMO and LUMO levels in correlation with the relative donating ability of the donor monomer. P9BF-OF has a reduced LUMO level in comparison with P9BF. P9BF-DPP has a very low band gap (1.8eV), with absorption well into the near-IR region. To examine ways to make borafluorene more air stable, a series of borafluorenes bearing bismethylmethoxyphenyl (BMMP) ligands were investigated. Interestingly, ii bismethylmethoxyphenyl-borafluorene (BMMP-BF) exhibits an exceptionally large Stokes shift of 16000 cm-1. To extend the conjugation and change the Stokes shift, thiophene containing derivatives BMMP-BF-T, BMMP-BF-2T, and BMMP-BF-3T were synthesized. These thiophene containing compounds exhibited anomalous two wavelength fluorescence. During our fluoride titration experiments, we noticed spectral im…
author: Adams, Ian
language: en_US
language: English
keywords: Analytical chemistry
date published: 2017
date modified: 2026-07-27T18:44:09Z
provider: University of Alabama
publisher: Networked Digital Library of Theses and Dissertations
type: WebPage
source organization: University of Alabama Libraries