Synthesis, mesomorphism and fluorescence of triphenylene-Bodipy dyads

Fang, Xiaoting; Guo, Hongyu; Lin, Jianrong; Yang, Fafu

doi:10.1016/j.tetlet.2016.09.082

Cited by 31 publications

(10 citation statements)

References 52 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Yang and co‐workers have prepared DLCs based on the triphenylene‐bodipy dyads and investigated their photophysical properties. These mesogens exhibited strong fluorescence properties along with a high quantum yields in solution and weak fluorescence in film . They have also reported triphenylene‐perylene‐triphenylene discotic triads along with bay substituents, which exhibit Col h phase over a broad range of temperature and photophysical properties .…”

Section: Introductionmentioning

confidence: 95%

Charge Transport in Novel Phenazine Fused Triphenylene Supramolecular Systems

et al. 2018

View full text Add to dashboard Cite

Novel phenazine-fused triphenylene discotic liquid crystals (DLCs) tethered with alkanethiols and alkoxy chains are synthesized. The condensation of 4,5-dibromobenzene-1,2diamine with triphenylene-1,2-diquinone discotic core, followed by the reaction with alkanethiols gives heterocyclic phenazinefused triphenylene based DLCs. The intermediate dibromosubstituted phenazine and final alkanethiol substituted phenazine-fused triphenylene derivatives exhibit a wide range of stable enantiotropic hexagonal columnar phase, which was characterised by polarized optical microscopy (POM), differential scanning calorimetry (DSC) and X-ray diffraction (XRD) studies. We have also investigated the photophysical properties of all phenazine compounds using dilute solution of anhydrous chloroform. The charge carrier mobility was measured for one representative compound by time of flight method which revealed that phenazine-fused triphenylene discotic mesogen exhibits p-type (hole) mobility of the order of 10 À4 cm 2 V À1 s À1 . The novel mesogens reported here present a wide temperature stability with good charge mobility and optical properties. These mesogens have shown potential applications for solar cells, sensors, organic light emitting diodes and other electrooptical device applications.[a] A.

show abstract

Section: Introductionmentioning

confidence: 95%

Charge Transport in Novel Phenazine Fused Triphenylene Supramolecular Systems

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Some D-A DLCs yield dual pathways along molecular columns to transfer electrons and holes [34,35]. At present, the discogens used in these D-A DLCs are limited in triphenylene, anthraquinone, perylene and BODIPY derivatives [36][37][38][39][40][41][42].…”

Section: Introductionmentioning

confidence: 99%

Mesogenic complementary absorbing dyads based on porphyrin and perylene units

Kong

Gong

Dai

et al. 2018

J. Porphyrins Phthalocyanines

View full text Add to dashboard Cite

Five novel dyads, consisting of a tetraphenylporphyrine unit connected to a perylene monoimide diester unit via a flexible bridge -CONH-(CH 2 ) n -(n = 4, 6, 8, 10 and 12), have been synthesized. Their structures were characterized by 13 C and 1 H nuclear magnetic resonance spectroscopy, infrared spectroscopy, mass spectrometry and elemental analysis. The UV-vis absorption spectra revealed these dyads have broad optical absorption in the ultraviolet and visible regions due to the complementary absorption of the two units. The differential scanning calorimetry traces and polarized optical microscopy textures showed all these dyads have columnar liquid crystal phases. Cyclic voltammetry revealed the highest occupied molecular orbitals of the dyads located on the porphyrin units, and the lowest unoccupied molecular orbitals located on the perylene units. In addition, these results were in agreement with that of the theoretical modeling. When excited at 423 or 473 nm, the photoluminescent emission spectra showed that the degree of fluorescence quenching of porphyrin units increased as the spacers became shorter. This quenching was ascribed to intramolecular photoinduced electron transfer, which also induced the dyad molecules to form the charge-separated states. The charge-separated molecules were further confirmed by the photocurrent response curves. These behaviors of broad absorption of the ultraviolet-visible light, yielding the charge-separated states of the molecules when excited and the formation of columnar liquid crystal phase made these dyads candidates for single-component photovoltaic active materials.

show abstract

“…On the other‐hand, multialkynylbenzenes (M) are the most investigated system among the various discotic nematogens where the rotational freedom of ethynyl linkers avoid the stacking of the disks needed for the column formation and hence induce a N D phase . In order to have the desired LC structure and to work with hierarchical structure, dyads and triads of T and T/M/PE have been also explored . But the detailed structure of their self‐assembly is missing.…”

Section: Introductionmentioning

confidence: 99%

“…[16] In order to have the desired LC structure and to work with hierarchical structure, dyads and triads of T and T/M/ PE have been also explored. [17][18][19][20][21][22][23][24] But the detailed structure of their self-assembly is missing. In this report, we have demonstrated the highly resolved self-assembled LC structures of T-M and T-M-T systems ( Figure 1) which are based on their reconstructed electron density maps.…”

Section: Introductionmentioning

confidence: 99%

Highly Resolved Morphology of Room‐Temperature Columnar Liquid Crystals Derived from Triphenylene and Multialkynylbenzene Using Reconstructed Electron Density Maps

Gupta

Pal

2017

ChemistrySelect

View full text Add to dashboard Cite

This paper demonstrates highly resolved structure of the self‐assembly of dyad and triads constituted from triphenylene (T) and multialkynylbenzene (M) units linked via flexible alkyl spacers (n). Resolved structures of these systems are based on reconstructed electron density maps derived from X‐ray diffraction patterns. T‐M compound (dyad) exhibits columnar hexagonal (Colh) phase which is explained by its columnar layered structure. In contrast, T‐M‐T compounds (triads) with spacer lengths of n = 8 and 10 exhibited columnar oblique (Colob) mesophase whereas, the one with shortest spacer length, i. e., n = 6, showed a columnar oblique plastic (Colobp) phase. We also found that molecules are interdigitated within themselves for compounds having longer spacer lengths (n = 8 and 10). However, a side by side packing is observed for the compound with shortest alkyl spacer (n = 6).

show abstract

Synthesis, mesomorphism and fluorescence of triphenylene-Bodipy dyads

Cited by 31 publications

References 52 publications

Charge Transport in Novel Phenazine Fused Triphenylene Supramolecular Systems

Charge Transport in Novel Phenazine Fused Triphenylene Supramolecular Systems

Mesogenic complementary absorbing dyads based on porphyrin and perylene units

Highly Resolved Morphology of Room‐Temperature Columnar Liquid Crystals Derived from Triphenylene and Multialkynylbenzene Using Reconstructed Electron Density Maps

Contact Info

Product

Resources

About