Chiral thiophene derivatives with optimal two‐photon absorption in near‐infrared window I and II

Abstract

Thiophene derivatives are outstanding organic materials due to their wide spectral response, superior optoelectronic properties, and excellent environmental stability, which have attracted widespread attention in both theory and applications. However, their chiral analogues and corresponding chiroptical behaviors have been rarely investigated. Herein, a series of chiral thiophene derivatives are firstly designed by taking both optical chirality and two‐photon absorption (TPA) response into consideration, and are then investigated by modern analytical response theory. The calculated results demonstrate that these novel chiral thiophene derivatives show optimal TPA in the near‐infrared (NIR) window I and II, indicating that they are promising for biological applications. More importantly, they exhibit reasonable two‐photon circular dichroism (TPCD) signals, which are desirable candidates for chiral recognition regions. Furthermore, the calculations of orbital transitions shed light on that the intramolecular charge transfer plays an important role in their excellent TPA and TPCD behaviors in NIR regions.

Near-infrared dyes for two-photon absorption in the short-wavelength infrared: strategies towards optical power limiting

“…As an example, a series of polyenes incorporating thiophene rings, strong benzothiadiazole acceptors and chiral non-conjugated decorations was theoretically found to exhibit two-photon circular dichroism (2PCD) in the 1200-1300 nm range. 235…”