Molecular Packing and Solid-State Fluorescence of Alkoxy-Cyano Substituted Diphenylbutadienes:  Structure of the Luminescent Aggregates

Davis, Riju; Kumar, N. S. Saleesh; Abraham, Shibu; Suresh, Cherumuttathu H.; Rath, Nigam P.; Tamaoki, Nobuyuki; Das, Suresh

doi:10.1021/jp710352m

Cited by 163 publications

(106 citation statements)

References 95 publications

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“…Interestingly, a similar blue shift of the fluorescence maxima was also observed when heating a thin film of (2,1-a)-dispiro(3,4,5-trimethoxyphenylfluorene)-indenofluorene (see Figure S18 in the Supporting Information), which became nearly identical to its emission spectrum in solution (see Figure S9 in the Supporting Information). Similar changes in the solid-state fluorescence spectrum with temperature have been reported for butadiene derivatives [64][65][66] but in these examples, the monomer-like or excimer-like fluorescence come from specific "intermolecular packing", which may be modified with temperature. In a "herringbone" arrangement, minimal electronic coupling between molecules led to a monomer-like emission, whereas in a "brickstone" arrangement, molecular packing led to excimer-like fluorescence.…”

Section: Wwwchemeurjorgsupporting

confidence: 74%

Blue Emitting 3 π–2 Spiro Terfluorene–Indenofluorene Isomers: A Structure–Properties Relationship Study

Poriel

Rault‐Berthelot

Thirion

et al. 2011

Chemistry A European J

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Two novel terfluorenyl derivatives, 2,2'',7,7''-tetrakis(9,9-dioctyl-9H-fluoren-2-yl)dispiro[fluorene-9,11'-indeno-(2,1-a)-fluorene-12',9''-fluorene] ((2,1-a)-DST-IF) and 2,2'',7,7''-tetrakis(9,9-dioctyl-9H-fluoren-2-yl)dispiro- [fluorene-9,6'-indeno-(1,2-b)-fluorene-12',9''-fluorene] ((1,2-b)-DST-IF) have been synthesized by two different synthetic approaches. These terfluorenyl derivatives possess a different central indenofluorene core, namely (2,1-a)-indenofluorene or (1,2-b)-indenofluorene, which imposes two distinct geometry profiles, and different structural environments for the terfluorenyl fluorophores that translates into drastically different optical and electrochemical properties for (2,1-a)-DST-IF and (1,2-b)-DST-IF. These properties have been carefully studied through a combined experimental and theoretical approach. The (2,1-a)-DST-IF isomer has been successfully used as emitting layer in a blue single-layer small-molecule organic light-emitting diode (SMOLED) and appears as the first example of a blue emission arising from intramolecular terfluorenyl excimers. Regarding the importance of terfluorenyl derivatives in organic electronics, the present structure-properties relationship study, may open new avenues in the design of efficient blue fluorophores.

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Section: Wwwchemeurjorgsupporting

confidence: 74%

Blue Emitting 3 π–2 Spiro Terfluorene–Indenofluorene Isomers: A Structure–Properties Relationship Study

Poriel

Rault‐Berthelot

Thirion

et al. 2011

Chemistry A European J

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“…1,2 Apart from the conventional interactions like hydrogen bonds, salt bridges and hydrophobic interactions, 3,4 other weak nonconventional interactions like CHÁÁÁp, OHÁÁÁp, NHÁÁÁp, and CationÁÁÁp interactions also play vital roles in protein stability. [5][6][7][8][9][10][11] The high incidence of such noncovalent interactions in large biological systems along with their key roles in chemical [12][13][14] and biological recognition processes 15,16 has led to an increasing number of theoretical 17,18 and experimental studies 19,20 devoted to the quantification and characterization of such interactions. Although useful to a certain extent, an accurate experimental description of noncovalent interactions is difficult 21 despite the enormous progress made in experimental techniques in the last decades.…”

Section: Introductionmentioning

confidence: 99%

Comparison of aromatic NH···π, OH···π, and CH···π interactions of alanine using MP2, CCSD, and DFT methods

et al. 2010

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A comparison of the performance of various density functional methods including long-range corrected and dispersion corrected methods [MPW1PW91, B3LYP, B3PW91, B97-D, B1B95, MPWB1K, M06-2X, SVWN5, ωB97XD, long-range correction (LC)-ωPBE, and CAM-B3LYP using 6-31+G(d,p) basis set] in the study of CH···π, OH···π, and NH···π interactions were done using weak complexes of neutral (A) and cationic (A(+)) forms of alanine with benzene by taking the Møller-Plesset (MP2)/6-31+G(d,p) results as the reference. Further, the binding energies of the neutral alanine-benzene complexes were assessed at coupled cluster (CCSD)/6-31G(d,p) method. Analysis of the molecular geometries and interaction energies at density functional theory (DFT), MP2, CCSD methods and CCSD(T) single point level reveal that MP2 is the best overall performer for noncovalent interactions giving accuracy close to CCSD method. MPWB1K fared better in interaction energy calculations than other DFT methods. In the case of M06-2X, SVWN5, and the dispersion corrected B97-D, the interaction energies are significantly overrated for neutral systems compared to other methods. However, for cationic systems, B97-D yields structures and interaction energies similar to MP2 and MPWB1K methods. Among the long-range corrected methods, LC-ωPBE and CAM-B3LYP methods show close agreement with MP2 values while ωB97XD energies are notably higher than MP2 values.

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“…[23][24][25][26][27][28][29][30][31][32][33][34][35] In this regard, small organic derivatives with olefin, acetylene, phenylenevinylene and phenyleneethynylene spacers have found current interest. 19,24,[36][37][38][39][40] Davis et al reported the solid state fluorescence of alkoxy-cyano substituted diphenylbutadiene derivatives. 24 Thomas et al described the photophysical properties of alkoxy substituted phenyleneethynylenes in the solid state.…”

mentioning

confidence: 99%

“…19,24,[36][37][38][39][40] Davis et al reported the solid state fluorescence of alkoxy-cyano substituted diphenylbutadiene derivatives. 24 Thomas et al described the photophysical properties of alkoxy substituted phenyleneethynylenes in the solid state. 40 The solid state fluorescence of some fluorinated diphenylpolyenes was reported by Sonoda et al 37 Lewis and Yang delineated the solid state fluorescence of some single olefin/acetylene spaced diphenyl derivatives with carboxamide substituents.…”

mentioning

confidence: 99%

Contrasting Solid-State Fluorescence of Diynes with Small and Large Aryl Substituents: Crystal Packing Dependence and Stimuli-Responsive Fluorescence Switching

2015

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There has been a significant current interest in solid state luminescence of organic molecules and their stimuli responsive fluorescence switching behavior. Although small organic derivatives with olefinic, acetylenic, phenylenevinylenic, phenyleneethynylenic spacers are widely documented as solid state emitters in the literature, the solid state photophysics of organic derivatives with "butadiyne" spacer still remains unexplored. We provide detailed investigation on the solid state fluorescence properties of a series of butadiynyl fluorophores. Replacement of a phenyl ring, which is at periphery of the butadiyne bridge, with a large moiety such as pyrenyl group furnishes contrasting emissions in the solid state. While the butadiyne bridged phenyl derivatives show a blue shift of emission maxima in the solid powder with respect to monomer spectra in solution state, the butadiyne bridged pyrenyl derivatives exhibit a red shift in the solid state. The blue shift of the emission maxima of the butadiyne bridged phenyl derivatives in the solid powder is attributed to allowed excitonic transition in aggregates with nearly parallel transition dipoles. On the other hand, formation of pyrenyl excimer accounts for the red shift of the butadiyne bridged pyrenyl derivatives in the solid powder. In addition to that, the solid state fluorescence of the pyrenyl analogues is reversibly switched between two aggregate forms through external heating and rubbing stimuli.

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Molecular Packing and Solid-State Fluorescence of Alkoxy-Cyano Substituted Diphenylbutadienes: Structure of the Luminescent Aggregates

Cited by 163 publications

References 95 publications

Blue Emitting 3 π–2 Spiro Terfluorene–Indenofluorene Isomers: A Structure–Properties Relationship Study

Blue Emitting 3 π–2 Spiro Terfluorene–Indenofluorene Isomers: A Structure–Properties Relationship Study

Comparison of aromatic NH···π, OH···π, and CH···π interactions of alanine using MP2, CCSD, and DFT methods

Contrasting Solid-State Fluorescence of Diynes with Small and Large Aryl Substituents: Crystal Packing Dependence and Stimuli-Responsive Fluorescence Switching

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