Details

Autor(en) / Beteiligte

• Harada, Mei
• Kutsuna, Misa
• Kitamura, Taichi
• Usui, Yusuke
• Ujiki, Masayoshi
• Nakamura, Yuka
• Obata, Tohru
• Tanioka, Masaru
• Uchiyama, Masanobu
• Sawada, Daisuke
• Kamino, Shinichiro

Titel

Nucleophile-Triggered π-Topological Transformation: a New Synthetic Approach to Near-Infrared-Emissive Rhodamines

Ist Teil von

• Chemistry : a European journal, 2023-10, Vol.29 (59), p.e202301969-e202301969

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2023

Quelle

Wiley Online Library

Beschreibungen/Notizen

• We describe a π-topological transformation-based synthetic method for the preparation of a new type of near-infrared (NIR)-emissive rhodamine dye called Polymethine-embedded Rhodamine Fluorophore (PeR Fluor). In contrast to conventional NIR-emissive dyes that require tedious synthetic steps and/or a high cost, linear fully π-conjugated PeR Fluor can be regioselectively prepared in one step by mixing different nucleophiles with ABPXs, a family of rhodamines with a cross-conjugated structure. PeR Fluor exhibits bright NIR fluorescence emission and high photostability owing to the cooperative π-electron system of rhodamines and polymethine scaffolds. Large bathochromic shifts of the absorption and fluorescence emission maxima can be achieved by modifying the N-substituted group to obtain NIR-absorbing/emitting PeR Fluor. We also demonstrate the stimulus-responsive functionality of PeR Fluor through the addition of chemicals (acid/base), which shows switchable NIR and visible fluorescence response. Our π-topological transformation-based synthetic method is a promising approach to produce new functionalized rhodamine dyes.