Photoinduced Intermolecular [4+2] Cycloaddition Reaction for Construction of Benzobicyclo[2.2.2]octane Skeletons

Liu, Qiang; Wang, Junlei; Li, Dazhi; Yang, Chao; Xia, Wujiong

doi:10.1021/acs.joc.6b02547

Cited by 6 publications

(4 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Photopolymerization usually occurs as fusion of highly reactive radical monomer units, which are produced by UV light irradiation, although new methods of photopolymerization are also rapidly being developed . The examples of photoinduced fusion include photoconjugation reactions between two molecules, such as cyclic α-diketones, benzobicyclo[2.2.2]octanes, polymers, etc., on one hand, and different CC containing compounds, on the other hand, which occur via [2 + 2], [4 + 2], or [4 + 4] photocycloaddition pathways. − The mechanism of [2 + 2] photocyclization between enones and alkenes begins with photoexcitation of the enone to a singlet excited state. The singlet state is typically very short-lived due to intersystem crossing to the triplet state.…”

Section: Birth Of Excitonsmentioning

confidence: 99%

Dynamics of Excitons in Conjugated Molecules and Organic Semiconductor Systems

Dimitriev

2022

Chem. Rev.

View full text Add to dashboard Cite

The exciton, an excited electron–hole pair bound by Coulomb attraction, plays a key role in photophysics of organic molecules and drives practically important phenomena such as photoinduced mechanical motions of a molecule, photochemical conversions, energy transfer, generation of free charge carriers, etc. Its behavior in extended π-conjugated molecules and disordered organic films is very different and very rich compared with exciton behavior in inorganic semiconductor crystals. Due to the high degree of variability of organic systems themselves, the exciton not only exerts changes on molecules that carry it but undergoes its own changes during all phases of its lifetime, that is, birth, conversion and transport, and decay. The goal of this review is to give a systematic and comprehensive view on exciton behavior in π-conjugated molecules and molecular assemblies at all phases of exciton evolution with emphasis on rates typical for this dynamic picture and various consequences of the above dynamics. To uncover the rich variety of exciton behavior, details of exciton formation, exciton transport, exciton energy conversion, direct and reverse intersystem crossing, and radiative and nonradiative decay are considered in different systems, where these processes lead to or are influenced by static and dynamic disorder, charge distribution symmetry breaking, photoinduced reactions, electron and proton transfer, structural rearrangements, exciton coupling with vibrations and intermediate particles, and exciton dissociation and annihilation as well.

show abstract

Section: Birth Of Excitonsmentioning

confidence: 99%

Dynamics of Excitons in Conjugated Molecules and Organic Semiconductor Systems

Dimitriev

2022

Chem. Rev.

View full text Add to dashboard Cite

show abstract

“…2,2'-(2,5-dihydroxy-1,4-phenylene)diacetic acid 1 and TPA-CHO were purchased in Aldrich and used as received. Ylide 3 [45] and TPA-Fu-CHO [46] were prepared as described in the literature.…”

Section: Synthesismentioning

confidence: 99%

Facile synthesis and optical properties of extended TPA-Benzodifuran derivatives connected by cyano-vinylene junctions

2018

View full text Add to dashboard Cite

Two new conjugated molecules based on triphenylaminebenzo [1,2-b:4,5-b']difuran moieties and integrating cyanovinyl bonds have been synthesized by using the new benzodifuran-acetonitrile synthon, easily and rapidly prepared in two steps from 2,2'-(2,5-dihydroxy-1,4-phenylene)diacetic acid. The electronic properties of the molecules were analysed by UV-Vis absorption and emission spectroscopies and cyclic voltammetry. The potential use of the molecules as donor materials for photovoltaic conversion were evaluated in simple bilayer solar cells using C60 as the acceptor materials. The comparison between the two derivatives reveals that the extension of the conjugated system with the insertion of furan cycles leads to a narrowing band gap, a better emission property, a direct access to dication state and an enhancement of the photovoltaic characteristics.

show abstract

“…It is noting that a highly stabilized biradical is an important resonance structure of o -QDM . Until now, the research on o -QDM mainly focused on the construction of polycyclic structures through Diels–Alder reaction, but the biradical resonance structure is less explored. In 1982, Saegusa and co-workers reported a mild generation of cyclic o -QDM intermediates, in which fluoride anion was mixed with [4-(trimethylsilyl)-1,2,3,4-tetrahydronaphth-1-yl] trimethylammonium iodide, and their dimerization reaction lead to binaphthyl derivatives .…”

Section: Introductionmentioning

confidence: 99%