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Development of Novel Intramolecular Charge Transfer Functional Dyes Based on Control of the Excited States

林 祐一朗 大阪府立大学 DOI:info:doi/10.24729/00017355

2021.04.21

概要

Charge transfer is one of the fundamental processes in many chemistry and biology [1]. Charge transfer processes can be divided into two categories. One is the charge transfer from an electron-rich donor molecule to a different electron-poor acceptor molecule, known as intermolecular charge transfer. The other is the charge transfer in the molecule containing the donor and the acceptor, generally called intramolecular charge transfer (ICT). The ICT process generally occurs upon the photoexcitation. The photoexcitation facilitates charge transfer from one part of a molecule in the ground state to another part in the excited state, resulting in the charge distribution in the excited state being significantly different from that in the ground state. Recently, π-conjugated organic molecules composed of electron donor (D) and acceptor (A) units (D–A-type ICT molecules, Fig. 1) have received a great deal of attention as a class of dyes exhibiting ICT behavior.

It is well known that D–A-type ICT molecules often give rise to dual emission. The peak found at the blue end of the emission spectrum is generally assumed to originate from the locally excited (LE) state, while the peak seen at the red end is generally assigned to the ICT excited species. The ICT process is promoted in polar solvents, and the large Stokes shift for the ICT fluorescence is due to electrostatic stabilization of the excited state by solvation [2]. In Fig. 2, the potential energy surface (PES) of the ground state S0 and the excited state S1 are illustrated for an ICT molecule, where both LE and ICT states are given for S1. In this scheme, the molecule is photoexcited and then subjected to relaxation to the LE state. The ICT reaction proceeds from the LE state to the ICT state across an activation energy barrier. This equilibrium between the LE and ICT states results in dual emission. Lippert et al. reported the dual emission of 4-N,N-dimethylaminobenzonitrile (DMABN) in 1962 [3]. The origin of the dual emission of DMABN had been discussed for several years, and finally, it was concluded that the double emission observed in DMABN was caused by the ICT in the excited state from the dimethylamino group to the cyano group upon photoexcitation. Subsequently, many related derivatives of DMABN have been reported to investigate the dynamics of the ICT process [4].

The early results of experimental and theoretical studies on the ICT process of DMABN suggest the twisted intramolecular charge transfer (TICT) [3]. In the TICT model, the ICT state is only generated by an adiabatic process from the LE state through rotational motion around the bond between the donor and acceptor subunits. In the absence of an energy barrier between the LE and ICT states, the relaxation of the excited state occurs very rapidly, leading to emission only from the ICT state. The TICT model had been recognized one of the common concepts in explaining the ICT process. However, there are many experimental results that cannot be explained by this model. For example, Yoshihara et al. reported that N-phenylpyrrole and its planar analogue (fluorazene phenylpyrrole), exhibit similar LE and ICT emission energies (Fig. 3) [5]. Hence, the planar intramolecular charge transfer (PICT) mechanism was proposed to explain these experimental results. There are several examples supporting the fact that the ICT state of the molecule does not have to be twisted [6].

ICT molecules form the molecular orbitals (MOs) extended over the entire D–A system by D–A interactions in the ground state (Fig. 4). The low bandgap transition induced by these MOs provides a broad electronic absorption band in the visible region. This transition is often called the ICT transition. The band gap of the ICT transition can be further reduced by extending the π-conjugation system between the donor and accepter moieties, as seen in a class of molecules called D–π–A type ICT molecules [7]. Molecules with D–A–D (or D–π–A–π–D) [8] and A–D– A (or A–π–D–π–A) [9] structures also belong to the group of ICT molecules, allowing us to design a wide range of functional dyes showing various photophysical properties. As shown above, ICT molecules exhibit specific and useful photophysical properties. Therefore, ICT functional dyes promise for applications such as nonlinear optical (NLO) materials [10], organic light emitting diodes (OLED) [8a,8c,11], solar energy conversion [7a,7b,9], and fluorescence sensing [12].

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