Discovery of dual fluorescent 1,8-naphthalimide dyes based on balanced seesaw photophysical model

Abstract

The 3 x 3 matrix elements included for the evaluation of dual fluorescence are based on a predictive model described as a 'seesaw balanced' photophysical model.

Single‐Molecular White‐Light Emitters and Their Potential WOLED Applications

“…Naphthalimide (NI) derivatives have been investigated as dual‐fluorescent dyes based on the strategy of introducing electron‐withdrawing group (EWG) on either naphthalene ring (acceptor) or phenyl ring (donor) to promote the HE emission. Conversely, a raise of the LE emission is observed when electron‐donating groups (EDGs) are added on both sides of NI . Therefore, panchromatic emission can be achieved via modifying the NI with EWGs (e.g., NO 2 and Cl) on the naphthalene moiety and EDG (e.g., NH 2 ) on the phenyl part 2‐(4‐aminophenyl)‐6‐chloro‐5‐nitro‐1 H ‐benzo[ f ]isoindole‐1,3(2 H )‐dione ( 56 ).…”

New core-substituted with electron-donating group 1,8-naphthalimides towards optoelectronic applications

“…The basic strategy for the synthesis of core-functionalized NIs usually starts from halogenated naphthalene dianhydride [12], [16], [20][21], [23][24]. In this work we explored the other possibility for core-modified NDI preparation based on utilization of naphthalene anhydride with nitro substituent at 3 core position.…”

“…Various core-functionalized both NDIs and NIs have been reported and wide is the range of possible their applications [11][12], [14][15], [17][18][19][20][21][22][23][24]. NIs have been investigated as fluorescent sensors for metal ions [25], light emitting compounds [12], [16], [26], electron-transporting materials [21], ambipolar semiconductors [20], colorimetric chemosensor [27], solvatochromic fluorophores [28], lightharvesting antennae [29], active aniti-bacterical dyes [30] and anticancer applications [31].…”

“…However, considering the literature data, more effective seem to be core-functionalization. The exploration of novel NDIs and NIs was motivated by the fact that an already low-lying LUMO can be further lowered by the incorporation of appropriate substituents to obtain air-stable electron transport materials [11] or efficient luminescent compounds [12][13][14][15][16]. Various core-functionalized both NDIs and NIs have been reported and wide is the range of possible their applications [11][12], [14][15], [17][18][19][20][21][22][23][24].…”

Synthesis and Photophysical Characterizations of Thermal -Stable Naphthalene Benzimidazoles

“…Highest quantum yield observed for NB_II (Φ f = 0.60). The presence of electron donating substituents may also increase the separation between the singlet (S 1 ) and its closer triplet excited state, thus decreasing the intersystem crossing (ISC) and favoring the fluorescence deactivation channel [24][25][26][27][28][29][30][31][32] (Figs. 5 and 6).…”