Pyrroloindole-Based Dynamic Combinatorial Chemistry

Tiberiu Gianga, Dora-Maria Rasadean, Dan Pantos

Research output: Contribution to journalArticlepeer-review

2 Citations (SciVal)


We report a new class of building blocks for Dynamic Combinatorial Chemistry (DCC) based on the pyrroloindole scaffold. The attachment of L-cysteine on the oc, a' positions of the core makes the molecule suitable for disulfide exchange in aqueous dynamic combinatorial libraries (DCLs). The synthesis or the core follows a modified version of the Knoevenagel-Hemetsberger approach. The new building block (l-PI) is fluorescent (Φ = 48%) and relatively stable towards thermal and photodegradation. The chirality of the cysteine is transferred to the electron-rich pyrroloindole core. Homo-and heterochiral DCLs of l-PI with electron-deficient l-and d-naphthalenediimide (NDI) lead to similar library distributions regardless of the enantiomer used. When no salt is present, the major component is a dimer, while dimers and tetramers are obtained at increased ionic strength.

Original languageEnglish
Article number726
Issue number5
Publication statusPublished - 3 May 2020

Bibliographical note

Funding Information:
Funding: This research was funded by EPSRC-DTP studentships to T.-M.G. and D.-M.R., grant numbers EB-CH1264 and EB-BB1250, respectively.

Publisher Copyright:
© 2020 by the authors.


  • Chirality
  • Disulfide
  • Dynamic combinatorial chemistry
  • Pyrroloindoles

ASJC Scopus subject areas

  • Computer Science (miscellaneous)
  • Chemistry (miscellaneous)
  • General Mathematics
  • Physics and Astronomy (miscellaneous)


Dive into the research topics of 'Pyrroloindole-Based Dynamic Combinatorial Chemistry'. Together they form a unique fingerprint.

Cite this