Thiochromenocarbazole imide: a new organic dye with first utility in large area flexible electroluminescent devices

Abstract

The N-annulation of a benzothioxanthene imide (BTI) derivative is demonstrated herein affording the unprecedented thiochromenocarbazole imide (TCI). The impact of this chemical modification on the molecular structure and optoelectronic properties...

The how and why of naphthalimide/heterocycle-fused hybrid dyes: an overview of the latest developments in the quest for dyes with innovative optical properties

“…3b). 12 Fig. 1 Structure of 4-amino-1,8-naphthalimide "4-ANI" and fused hybrids, including perylene diimides "PDIs", naphthalene diimides "NDIs" and general structures of ANI/heterocycle fused hybrid dyes.…”

“…This new example confirms that to date, the use of heteroxanthene/ANI-fused hybrid molecules is mostly considered for therapeutic applications, and examples from the literature also tend to assert that they are good candidates for bioelectronic applications. 10,12 For all the examples presented above, one can wonder what would be the impact on fluorescence of introducing an electron donating group (EDG) in a judiciously selected position of xanthene or heteroxanthene/ANI-fused hybrids, to allow the establishment of an internal charge transfer (ICT) between this EDG and the phthalimide unit electron-withdrawing group (EWG). I believe that this is a plausible and relevant method of reflection in the quest for fluorescent chromophores fusing an ANI backbone to a xanthene or heteroxanthene unit.…”

“…This new example confirms that to date, the use of heteroxanthene/ANI-fused hybrid molecules is mostly considered for therapeutic applications, and examples from the literature also tend to assert that they are good candidates for bioelectronic applications. 10,12…”

“…10 (b) Structure of thiochromenocarbazole imide TCI2 and photographs of flexible OLEDs. Figures adapted from the literature 12.…”

Systematic Investigation of Core and Endcap Selection on the Development of Functional π-Conjugated Materials

“…A class of synthetically versatile organic compounds, known as π-conjugated materials, have been extensively used for a number of applications including charge transport/extraction, − light emission, − and even small-molecule catalysis. − Among the numerous π-conjugated material designs, the arrangement of electron-deficient (acceptor) and electron-rich (donor) organic units in an acceptor–donor–acceptor (A–D–A) motif has been popularized owing to the fact that the optical band gap, electron affinity, and/or redox stability can be easily tuned . Generally speaking, improved semiconducting properties are observed in A–D–A systems with an extended π-orbital overlap; this can be achieved by materials that exhibit either a highly planar ring-fused organic backbone or by those that promote conformational locking interactions between heteroatom-containing functional groups in the organic backbone. − ,, While nearly an infinite number of specialized organic building blocks may be pieced together to make these A–D–A π-conjugated materials, it is important that a reliable, selective, efficient, and atom-economical synthetic protocol be developed for these materials to ever be produced on the industrial scale. , With these criteria in mind, the use of direct (hetero)­arylation (DHA) to develop these π-conjugated materials has been leveraged as a highly effective cross-coupling method.…”