Photophysical properties of 1,8-naphthalic anhydride in aprotic solvents: An electron acceptor in excited state

Ghosh, Sujay; Biswas, Subhanip; Mondal, Mousumi; Basu, Samita

doi:10.1016/j.jlumin.2013.07.057

Cited by 5 publications

(7 citation statements)

References 27 publications

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“…These bands can be safely ascribed to the naphthalimide anion, since the spectrum of NI‐am obtained by spectroelectrochemistry (Figure S46) clearly evidences their presence together with an intense peak at ca. 420 nm, usually reported for NI anions . The radical cation of 1,2‐dimethoxybenzene, that can be considered as a model for the DB24C8 ring, has been reported to show absorption features at ca.…”

Section: Resultsmentioning

confidence: 99%

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Photoinduced Electron Transfer Involving a Naphthalimide Chromophore in Switchable and Flexible [2]Rotaxanes

Colasson

Ventura

2019

Chemistry A European J

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The interlocking of ring and axle molecular components in rotaxanes provides a way to combine chromophoric, electron‐donor and electron‐acceptor moieties in the same molecular entity, in order to reproduce the features of photosynthetic reaction centers. To this aim, the photoinduced electron transfer processes involving a 1,8‐naphthalimide chromophore, embedded in several rotaxane‐based dyads, were investigated by steady‐state and time‐resolved absorption and luminescence spectroscopic experiments in the 300 fs–10 ns time window. Different rotaxanes built around the dialkylammonium/ dibenzo[24]crown‐8 ether supramolecular motif were designed and synthesized to decipher the relevance of key structural factors, such as the chemical deactivation of the ammonium‐crown ether recognition, the presence of a secondary site for the ring along the axle, and the covalent functionalization of the macrocycle with a phenothiazine electron donor. Indeed, the conformational freedom of these compounds gives rise to a rich dynamic behavior induced by light and may provide opportunities for investigating and understanding phenomena that take place in complex (bio)molecular architectures.

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Section: Resultsmentioning

confidence: 99%

“…420 nm, usually reported for NI anions. [31,[48][49][50] The radicalc ation of 1,2-dimethoxybenzene, that can be considered as am odel fort he DB24C8 ring, has been reported to show absorption features at ca. 400-430 nm, ar egion outside the spectral range of our analysis.…”

Section: Transient Absorption Spectroscopymentioning

confidence: 99%

Photoinduced Electron Transfer Involving a Naphthalimide Chromophore in Switchable and Flexible [2]Rotaxanes

Colasson

Ventura

2019

Chemistry A European J

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“…11 No experimental data are available on the excited states of isolated NDCA, but UV/vis spectra in a number of different solvents yielded the first absorption bands between 338 and 350 nm. 16 Thus, after excitation of the NDCA S 1 state a two-photon ionization step is required for ionization. The [1 + 2′] resonance-enhanced multiphoton ionization (REMPI-) spectrum of NDCA is depicted in Figure 3.…”

Section: ■ Resultsmentioning

confidence: 99%

“…The ionization energy (IE) of NDCA in the gas phase was determined to be 8.98 eV by photoelectron spectroscopy . No experimental data are available on the excited states of isolated NDCA, but UV/vis spectra in a number of different solvents yielded the first absorption bands between 338 and 350 nm . Thus, after excitation of the NDCA S 1 state a two-photon ionization step is required for ionization.…”

Section: Resultsmentioning

confidence: 99%

“…15 In a previous solution phase study a fluorescence lifetime τ rad = 1.3 ns was found for NDCA in benzene. 16 Notwithstanding the lack of data for the isolated NDCA molecule, its derivatives are of considerable interest from an applicational point of view since they can be used as dyes, in liquid crystal displays, or in organic light-emitting diodes. 17…”

Section: ■ Introductionmentioning

confidence: 99%

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Time-Resolved Study of 1,8-Naphthalic Anhydride and 1,4,5,8-Naphthalene-tetracarboxylic Dianhydride

et al. 2015

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We investigate the excited electronic states of 1,8-naphthalic anhydride (NDCA) and 1,4,5,8-naphthalene-tetracarboxylic dianhydride (NTCDA) by time- and frequency-resolved electronic spectroscopy in the gas phase using picosecond lasers and by femtosecond time-resolved transient absorption in cyclohexane. The experiments are accompanied by calculations that yield the energy of the excited singlet and triplet states as well as by surface hopping dynamics simulations and calculations of spin-orbit couplings that give insight into the photochemistry. The origin of the A (1)A1 ← X (1)A1 (ππ*) transition in isolated NDCA was found at 30 260 cm(-1), and several low-lying vibrational bands were observed. The lifetime drops sharply from 1.2 ns at the origin to around 30 ps at an excess energy of 800 cm(-1). Both internal conversion (IC) and intersystem crossing (ISC) are possible deactivation pathways as found in coupled electron-nuclear dynamics simulations. In cyclohexane solution, two time constants were observed. Deactivation of the initially excited state by ISC seems to dominate as supported by computations. For NTCDA we observed a gas phase lifetime of 16 ps upon excitation at 351 nm.

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Efficient Host‐Guest Complexation of a Bisporphyrin Host with Electron Deficient Guests: Synthesis, Structure, and Photoinduced Electron Transfer

Mondal

Rath

2015

Israel Journal of Chemistry

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The encapsulation of 1,8‐naphthalic anhydride (NAN), 9‐dicyanomethylenefluorene (9‐DCF), acenaphthenequinone (ANQ), and 4‐chloro‐7‐nitrobenzofurazan (NBD‐Cl) by diethylpyrrole‐bridged bisporphyrin (H4DEP) and its dizinc(II) analogue (Zn2DEP) are employed to investigate the structural and spectroscopic changes within the bisporphyrin cavity upon substrate binding. Synthesis and X‐ray structures of all four encapsulated host‐guest complexes (H4DEP⋅NAN, H4DEP⋅9‐DCF, Zn2DEP⋅ANQ, and Zn2DEP⋅NBD‐Cl) are reported here. The binding constant calculations show strong 1 : 1 binding between the hosts (H4DEP and Zn2DEP) and the guests (NAN/9‐DCF/ANQ/NBD‐Cl). 1H‐NMR spectra also support the retention of the host‐guest assemblies in solution. Negative and positive shifts of the reduction and oxidation potentials, respectively, indicate that it is difficult to reduce/oxidize the encapsulated complexes. The emission intensities of the bisporphyrins (H4DEP and Zn2DEP) are substantially quenched in all the complexes, owing to photoinduced electron transfer from the excited state of the bisporphyrins to guest molecules. All the experimental evidence is further substantiated by DFT calculations. Such an efficient electron transfer is only possible when the donor and the acceptor moieties are in close propinquity to each other, which eventually lowers the reorganization energy.

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Photophysical properties of 1,8-naphthalic anhydride in aprotic solvents: An electron acceptor in excited state

Cited by 5 publications

References 27 publications

Photoinduced Electron Transfer Involving a Naphthalimide Chromophore in Switchable and Flexible [2]Rotaxanes

Photoinduced Electron Transfer Involving a Naphthalimide Chromophore in Switchable and Flexible [2]Rotaxanes

Time-Resolved Study of 1,8-Naphthalic Anhydride and 1,4,5,8-Naphthalene-tetracarboxylic Dianhydride

Efficient Host‐Guest Complexation of a Bisporphyrin Host with Electron Deficient Guests: Synthesis, Structure, and Photoinduced Electron Transfer

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