From 2,5-Diformyl-1,4-dihydropyrrolo[3,2- b]pyrroles to Quadrupolar, Centrosymmetric Two-Photon-Absorbing A-D-A Dyes

Paweł Kowalczyk; Mariusz Tasior; Shuhei Ozaki; Kenji Kamada; Daniel T Gryko

doi:10.1021/acs.orglett.2c00718

From 2,5-Diformyl-1,4-dihydropyrrolo[3,2- b]pyrroles to Quadrupolar, Centrosymmetric Two-Photon-Absorbing A-D-A Dyes

Org Lett. 2022 Apr 8;24(13):2551-2555. doi: 10.1021/acs.orglett.2c00718. Epub 2022 Mar 28.

Authors

Paweł Kowalczyk¹, Mariusz Tasior¹, Shuhei Ozaki^{2

3}, Kenji Kamada^{2

3}, Daniel T Gryko¹

Affiliations

¹ Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
² NMRI, National Institute of Advanced Industrial Science and Technology (AIST), Ikeda, Osaka 563-8577, Japan.
³ Department of Chemistry, Graduate School of Science and Technology, Kwansei Gakuin University, Sanda 669-1337, Japan.

Abstract

An original approach has been developed for the insertion of formyl substituents at positions 2 and 5 of 1,4-dihydropyrrolo[3,2-b]pyrroles by conversion of thiazol-2-yl substituents. The synthetic utility of these formyl groups was investigated, and a series of centrosymmetric A-π-D-π-A frameworks were constructed. The two-photon absorption of the quadrupolar pyrrolo[3,2-b]pyrrole possessing two dicyanovinylidene flanking groups is attributed to an S₀ → (S₁) → S₄ transition which has a large TPA cross-section (1300 GM) for a molecule of this size.