---
OA_type: closed access
_id: '21816'
abstract:
- lang: eng
  text: 'A new Diels−Alder (DA)-based photopatterning platform is presented, which
    exploits the irreversible, light-induced decarbonylation and subsequent cleavage
    of cyclopentadienone−norbornadiene (CPD−NBD) adducts. A series of CPD−NBD adducts
    have been prepared and systematically studied toward the use in a polymeric material
    photopatterning platform. By incorporating an optimized CPD−NBD adduct into polymer
    networks, it is demonstrated that cyclopentadiene may be unveiled upon 365 nm
    irradiation and subsequently clicked to a variety of maleimides with spatial control
    under mild reaction conditions and with fast kinetics. Unlike currently available
    photoinduced Diels−Alder reactions that rely on trapping transient, photocaged
    dienes, this platform introduces a persistent, yet highly reactive diene after
    irradiation, enabling the use of photosensitive species such as cyanine dyes to
    be patterned. To highlight the potential use of this platform in a variety of
    material applications, we demonstrate two proof-of-concepts: patterned conjugation
    of multiple dyes into apolyacrylate network and preprogrammed ligation of streptavidin
    into poly(ethylene glycol) hydrogels.'
article_processing_charge: No
article_type: original
author:
- first_name: Sophia J.
  full_name: Bailey, Sophia J.
  last_name: Bailey
- first_name: Friedrich J
  full_name: Stricker, Friedrich J
  id: 7aca2cfc-46cf-11f0-abd3-8c96b5186745
  last_name: Stricker
- first_name: Erik
  full_name: Hopkins, Erik
  last_name: Hopkins
- first_name: Maxwell Z.
  full_name: Wilson, Maxwell Z.
  last_name: Wilson
- first_name: Javier
  full_name: Read de Alaniz, Javier
  last_name: Read de Alaniz
citation:
  ama: Bailey SJ, Stricker FJ, Hopkins E, Wilson MZ, Read de Alaniz J. Shining light
    on cyclopentadienone–norbornadiene Diels-Alder adducts to enable photoinduced
    click chemistry with cyclopentadiene. <i>ACS Applied Materials &#38; Interfaces</i>.
    2021;13(30):35422-35430. doi:<a href="https://doi.org/10.1021/acsami.1c08670">10.1021/acsami.1c08670</a>
  apa: Bailey, S. J., Stricker, F. J., Hopkins, E., Wilson, M. Z., &#38; Read de Alaniz,
    J. (2021). Shining light on cyclopentadienone–norbornadiene Diels-Alder adducts
    to enable photoinduced click chemistry with cyclopentadiene. <i>ACS Applied Materials
    &#38; Interfaces</i>. American Chemical Society. <a href="https://doi.org/10.1021/acsami.1c08670">https://doi.org/10.1021/acsami.1c08670</a>
  chicago: Bailey, Sophia J., Friedrich J Stricker, Erik Hopkins, Maxwell Z. Wilson,
    and Javier Read de Alaniz. “Shining Light on Cyclopentadienone–Norbornadiene Diels-Alder
    Adducts to Enable Photoinduced Click Chemistry with Cyclopentadiene.” <i>ACS Applied
    Materials &#38; Interfaces</i>. American Chemical Society, 2021. <a href="https://doi.org/10.1021/acsami.1c08670">https://doi.org/10.1021/acsami.1c08670</a>.
  ieee: S. J. Bailey, F. J. Stricker, E. Hopkins, M. Z. Wilson, and J. Read de Alaniz,
    “Shining light on cyclopentadienone–norbornadiene Diels-Alder adducts to enable
    photoinduced click chemistry with cyclopentadiene,” <i>ACS Applied Materials &#38;
    Interfaces</i>, vol. 13, no. 30. American Chemical Society, pp. 35422–35430, 2021.
  ista: Bailey SJ, Stricker FJ, Hopkins E, Wilson MZ, Read de Alaniz J. 2021. Shining
    light on cyclopentadienone–norbornadiene Diels-Alder adducts to enable photoinduced
    click chemistry with cyclopentadiene. ACS Applied Materials &#38; Interfaces.
    13(30), 35422–35430.
  mla: Bailey, Sophia J., et al. “Shining Light on Cyclopentadienone–Norbornadiene
    Diels-Alder Adducts to Enable Photoinduced Click Chemistry with Cyclopentadiene.”
    <i>ACS Applied Materials &#38; Interfaces</i>, vol. 13, no. 30, American Chemical
    Society, 2021, pp. 35422–30, doi:<a href="https://doi.org/10.1021/acsami.1c08670">10.1021/acsami.1c08670</a>.
  short: S.J. Bailey, F.J. Stricker, E. Hopkins, M.Z. Wilson, J. Read de Alaniz, ACS
    Applied Materials &#38; Interfaces 13 (2021) 35422–35430.
date_created: 2026-05-06T10:54:16Z
date_published: 2021-07-26T00:00:00Z
date_updated: 2026-05-12T09:49:57Z
day: '26'
ddc:
- '540'
doi: 10.1021/acsami.1c08670
extern: '1'
external_id:
  pmid:
  - '34310127'
fulldoi: https://doi.org/10.1021/acsami.1c08670
intvolume: '        13'
issue: '30'
keyword:
- click chemistry
- Diels−Alder
- cyclopentadiene
- photochemistry
- photopatterning
language:
- iso: eng
month: '07'
oa_version: None
page: 35422-35430
pmid: 1
publication: ACS Applied Materials & Interfaces
publication_identifier:
  eissn:
  - 1944-8252
  issn:
  - 1944-8244
publication_status: published
publisher: American Chemical Society
quality_controlled: '1'
scopus_import: '1'
status: public
title: Shining light on cyclopentadienone–norbornadiene Diels-Alder adducts to enable
  photoinduced click chemistry with cyclopentadiene
type: journal_article
user_id: ba8df636-2132-11f1-aed0-ed93e2281fdd
volume: 13
year: '2021'
...